Pigment dispersing agent

ABSTRACT

A pigment dispersing agent for paints is a combination of particular amine compound and particular acrylic copolymer or a combination of particular amine compound, particular acrylic copolymer and particular polyester resin. This pigment dispersing agent is applicable to both acrylic resin series paints and polyester resin series paints.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to a pigment dispersing agent used when a pigmentis mixed with a coating composition in the manufacture of paints.

2. Related Art Statement

In the manufacture of paints, it is important to mix the pigment withthe coating composition. In this case, the pigment to be usually used inthe paint is dispersed into only a part of a vehicle constituting thepaint together with a proper solvent, diluent or other additive by meansof a mill used in the paint industry to obtain a dispersion paste. Then,this paste is mixed with the remaining amount of the vehicle and othernecessary additives to obtain a pigment dispersing composition as apaint. However, the greatest problem of such a pigment dispersingcomposition lies in that the pigment particles are apt to beagglomerated. As a result, it is known to cause unfavorable phenomenasuch as decrease of paint stability, occurrence of troubles in thepainting, reductions of color strength, gloss and distinctness of imageof the finally obtained paint film, flooding, floating, color changewith time and the like Such a phenomenon that the pigment particles areapt to be agglomerated is explained by London - van der Waals forceattracting the particles to each other. In order to overcome thisattracting force, it is necessary to provide an adsorption layer ontothe surface of the particle, and consequently various methods areattempted. For instance, there are known (1) a method of dispersing thepigment by using non-ionic, anionic or cationic surfactant, or a wettingagent such as aliphatic polyvalent carboxylic acid or the like as anassistant; (2) a method of mixing the pigment with a certain substitutedderivative of the pigment as disclosed in Japanese Patent laid open No.51-18,736; (3) a method of dispersing the pigment by using a highmolecular weight dispersing agent obtained by the bonding of a basicsubstance and a polyester compound as disclosed in Japanese Patent laidopen No. 60-166,318 and No. 61-174,939; (4) a method of dispersing thepigment by using a high molecular weight dispersing agent obtainedthrough the bonding of a basic substance and an acrylic polymer asdisclosed in Japanese Patent laid open No. 46-7,294; and the like.

In the dispersion assistant used in the method (1), however, theadsorption layer adsorbed on the particle surface is thin and does notdevelop the satisfactory stabilizing effect and hence the pigmentdispersing performances are not observed. The pigment derivative used inthe method (2) is naturally colored, so that it can not generally beused for various pigments. The basic thought of the dispersing agentused in the methods (3) and (4) is a technical idea of making a blockstructure from a polymer portion capable of solvating with a solvent andan anchor portion adsorbed on the pigment as described by A. Topham inProgress in Organic Coatings, vol. 5, (1977) pp 237-243. In thistechnique, it is important that the polymer portion capable of solvatingwith the solvent is excellent in the compatibility with a resin added asa film forming component of the paint film and the adsorption state ofthe dispersing agent to the pigment is tail-like. If the polymer portioncapable of solvating with the solvent is poor in the compatibility withthe resin added as the film forming component of the paint film, thesolvated polymer portion agglomerates to cause the degradation ofpigment dispersing performances.

In the dispersing agent used in the method (3), therefore, when thecompatibility between the dispersing agent and the dispersion vehicle isgood, the remarkable improvement of the pigment dispersing performancesis observed, but when using the dispersion vehicle having a poorcompatibility, the protective layer for the dispersing agent adsorbed onthe particle surface agglomerates to undesirably degrade the pigmentdispersing performances. Especially, since the dispersing agent consistsmainly of polyester compound, it is poor in compatibility with anacrylic resin or the like important as a painting resin, so that it isdifficult to obtain good pigment dispersing performances in case ofacrylic resin series paints. Furthermore, the polyester portion of thisdispersing agent has no functional group reacting with a curing agent inthe paint such as melamine resin, urea resin, polyisocyanate resin orthe like, it acts as a plasticizer in the paint film to causedegradation of weather resistance, humidity resistance and the like inthe paint film and the local floating of the pigment dispersing agentonto the surface of the paint film after the curing of the paint orso-called bleeding phenomenon, whereby the gloss and hardness arelowered. Moreover, when the dispersing agent is used for multilayercoating, is caused after trouble adhesion trouble between the paintfilms due to the presence of the bled component and the like.

On the other hand, the pigment dispersing agent used in the method (4)serves for ordinary acrylic resin series paints because acrylic resin isused as a polymer portion. However, the polymer portion has no reactionpoint such as hydroxyl group, carboxyl group or the like reacting with acrosslinking agent like the method (3) and is not chemically fixed inthe paint film, so that there is a problem of damaging the quality ofpaint film due to the plasticizer action as previously mentioned.

Furthermore, in the method (4), all of the polymer portion is comprisedof acrylic resin, so that it is difficult to be used for polyester resinseries paints.

In both methods (3) and (4), since the polymer portion has no polargroup such as hydroxyl group, carboxyl group or the like, it is poor incompatibility with a resin having a relatively high polarity, so that itis difficult to utilize these methods in paints consisting mainly ofsuch a resin and hence the application range thereof is critical.

SUMMARY OF THE INVENTION

Under the above circumstances, the inventors have made studies withrespect to (1) a pigment dispersing agent capable of widely utilizing inacrylic resin series paints usually used in the art and simultaneouslyfixing in the paint film through the curing reaction with an amino resinsuch as melamine resin, urea resin and also with polyisocyanate resin orthe like; and (2) a pigment dispersing agent capable of utilizing inpolyester resin series paints in addition to the acrylic resin seriespaint and fixing in the paint film through the reaction with acrosslinking agent such as amino resin, polyisocyanate resin or thelike, and as a result the invention has been accomplished.

That is, the invention provides pigment dispersing agents of thefollowing first and second inventions. I. A pigment dispersing agentconsisting of a product obtained by reacting the following component A₁with the following component B at a mol ratio of component A₁ tocomponent B of 1:1-1:40.

Component A₁ : an amine compound containing one or more amino groupand/or imino group in its molecule and having a weight average molecularweight of 60-30,000 and an amine value of 50-2,000 mg KOH/g;

Component B: an acrylic copolymer having a weight average molecularweight of 2,000-100,000 and a hydroxyl value of 5-200 and containing oneof glycidyl group ##STR1## acetoacetoxy group (--O--CO--CH₂ --CO--CH₃,component B₂) and cyclocarbonate group ##STR2## in a functional groupnumber of 0.7-3.0 on average per molecule as a side chain, provided that1 mole of glycidyl group is considered to be 1 mol of hydroxyl group inthe calculation of hydroxyl value. II. A pigment dispersing agentconsisting of a product obtained by reacting the following component A₂and component B with one of the following six components C at a molratio of component A₂ to component B to component C of 1:1:1-1:40:40.

Component A₂ : an amine compound containing one or more amino group ortwo or more imino group or one or more amino and imino groups in itsmolecule and having a weight average molecular weight of 60-30,000 andan amine value of 50-2,000 mg KOH/g;

Component B: an acrylic copolymer having a weight average molecularweight of 2,000-100,000 and a hydroxyl value of 5-200 and containing oneof glycidyl group ##STR3## acetoacetoxy group (--O--CO--CH₂ --CO--CH₃,component B₂) and cyclocarbonate group ##STR4## in a functional groupnumber of 0.7-3.0 on average per molecule as a side chain, provided that1 mole of glycidyl group is considered to be 1 mol of hydroxyl group inthe calculation of hydroxyl value;

Component C: a polyester resin of the following structures having aweight average molecular weight of 1,000-30,000 and containingisocyanate group or acetoacetoxy group in its terminal

    R.sub.1 --O--(CO--R.sub.2 --O).sub.n --CO--NH--R.sub.3 --NCO (C.sub.1)

    R.sub.1 --O--(CO--R.sub.2 --O).sub.n --CO--CH.sub.2 CO--CH.sub.3 (C.sub.2)

    R.sub.1 --O--(CO--R.sub.4 --COO--CHR.sub.5 --CHR.sub.6 --O).sub.n --CO--NH--R.sub.3 --NCO                                   (C.sub.3)

    R.sub.1 --O--(CO--R.sub.4 --COO--CHR.sub.5 --CHR.sub.6 --O).sub.n --CO--CH.sub.2 --CO--CH.sub.3                             (C.sub.4)

    R.sub.1 --CO--()--CHR.sub.5 --CHR.sub.6 --O--COR.sub.4 --CO).sub.n --O--CHR.sub.5 --CHR.sub.6 --OCO--NH--R.sub.3 --NCO       (C.sub.5)

    R.sub.1 --CO--(O--CHR.sub.5 --CHR.sub.6 --O--O--COR.sub.4 --CO).sub.n --O--CHR.sub.5 --CHR.sub.6 --OCO--CH.sub.2 COCH.sub.3     (C.sub.6)

R₁ : aliphatic, alicyclic or aromatic hydrocarbon group having a carbonnumber of 1-18,

R₂ : alkylene group having a carbon number of 1-7,

R₃ : residual group of aliphatic, alicyclic or aromatic diisocyanatehaving a carbon number of 6-20,

R₄ : Residual group of aliphatic, alicyclic or aromatic acid anhydridehaving a carbon number of 2-20,

R₅, R₆ : hydrogen atom, aliphatic, alicyclic or aromatic hydrocarbongroup having a carbon number of 1-20, --CH₂ --O--R₁ group or --CH₂--OCO--R₁ group

n: an integer of 1 or more.

Moreover, when it is not required to divide components A, B and C intocomponents A₁ and A₂, components B₁ -B₃ and components C₁ -C₆ in thefollowing explanation, these components are abbreviated as components A,B and C.

In the first invention, the amine compound of the component A isstrongly adsorbed on the surface of the pigment, and the acrylic resinof the component B is excellent in the compatibility with the acrylicresin as a vehicle and forms a stable and sterically repulsive layer toprevent the agglomeration of the pigment particles. Furthermore, sincethe acrylic resin of the component B has a hydroxyl group in its sidechain, it is chemically fixed in the paint film at the curing step ofthe paint film.

In the second invention, the polyester resin of the component C isfurther incorporated in addition to the components A₂ and B, so that thecompatibility with the polyester series resin is ensured besides themerits of the first invention, and the resulting pigment dispersingagent acts to both acrylic and polyester resin paints.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The pigment dispersing agents according to the invention will bedescribed in detail below.

The component A₁ used in the first invention is an amine compoundcontaining one or more amino group and/or imino group in the moleculefor providing a bonding point to the component B and having a weightaverage molecular weight of 60-30,000 and an amine value of 50-2,000 mgKOH/b. The component A₁ may include a tertiary amine group. Thecomponent A₂ used in the second invention is an amine compoundcontaining one or more amino group or two or more imino group or one ormore amino and imino groups for providing bonding points to bothcomponents B and C and having a weight average molecular weight of60-30,000 and an amine value of 50-2,000 mg KOH/g. The component A₂ mayinclude a tertiary amine group.

When the weight average molecular weight of the component A is less than60, the adsorption force to the pigment is weak and the pigmentdispersing performances are degraded, while when it exceeds 30,000 thecompatibility with the resin becomes poor and further the adsorptiongroup becomes too long and hence the component A may act as anagglomerating agent to degrade the pigment dispersing performances. Whenthe amine value of the component A is less than 50 mg KOH/g, theadsorbing force is insufficient and the dispersibility is poor, whilewhen it exceeds 2,000 mg KOH/g, the water resistance and weatherresistance of the paint film are injured.

The amine compound as the component A has any molecular structure suchas straight chain, branched chain, ring and the like. For example, asthe component A₁, mention may be made of alkylamines represented by NH₂(CH₂)_(n) CH₃ provided that n≧1 such as ethylamine, propylamine,butylamine, pentylamine, hexylamine, heptylamine, octylamine,nonylamine, decylamine and the like; and alkylimines being isomers ofthe above alkylamines and containing imino group. As the components A₁,A₂, mention may be made of diamines represented by NH₂ (CH₂)_(n) NH₂provided that n≧2 such as ethylenediamine, propylenediamine,tetramethylene diamine, pentamethylene diamine, hexamethylene diamine,heptamethylene diamine, octamethylene diamine and the like; alkylpolyamines such as 1,2,3-triamino propane, tris (2-aminoethyl) amine,tetra (aminomethyl) methane, iminobispropyl amine, methyliminobispropylamine, N-methylethylene diamine, N-ethylethylene diamine and the like;polyethylene imines represented by NH₂ (CH₂ CH₂ NH)_(n) CH₂ CH₂ providedthat n≧1 such as diethylene triamine, triethylene tetramine,tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine,heptaethylene octamine, octaethylene nonamine, nonaethylene decamine andtrade names of Montrec (made by Dow Chemical Co.), Polymine Waterflow(made by BASF AG) and Epomine (made by Nippon Shokubai Kagaku KogyoK.K.); polyalkyl polyamines obtained by dehydrochlorination reaction ofdihalides of chain or ring hydrocarbons having a carbon number of 1-8with ammonia or organic amines containing chain or ring hydrocarbongroup having a carbon number of 1-8; cyclodialkylene diimines such as1,4-diazacyclo heptane, cyclo di(trimethylene) diimine, cyclodi(heptamethylene) diimine, cyclo di(octamethylene) diimine and thelike; aromatic amines such as m-xylenediamine, m-toluylene diamine,dianisidine, p-phenylene diamine, 3,5-dichloro-4,4-diaminodiphenylmethane and the like; heterocyclic amines such as N-aminopropylmorpholine, 1-(2-aminoethyl) piperazine, 4-amino-2-methoxy-pyrimidine,4-(aminoethyl) pyridine, 2-amino-6-methoxy benzothiazole, N,N-diallylmelamine, benzoguanamine, acetoguanamine, 3-amino-1,2,4-triazole,1-aminoethyl piperazine, melamine and the like; and dimethyl aminopropylamine, diethyl aminopropyl amine, morpholine, 1-(2-hydroxyethyl)piperamine, 1-(3-aminopropyl) imidazole, 1,2-(hydroxyethyl) imidazoleand the like.

The component B used in the invention is an acrylic copolymer having aweight average molecular weight of 2,000-100,000 and a hydroxyl value of5-200 and containing one of glycidyl group, acetoacetoxy group andcyclocarbonate group as a side chain at a functional group number of0.7-3.0 per molecule. When the weight average molecular weight is lessthan 2,000, the sufficient, sterically repulsive layer is not formed andthe pigment dispersing performances are degraded, while when it exceeds100,000, the pigment dispersing agent is apt to be desorbed from thesurface of the pigment and the pigment dispersing performances aredegraded. When the hydroxyl value is less than 5, the amount acting as acrosslinking point for the crosslinking agent is insufficient and thepigment dispersing agent derived from the component B is not fixed inthe paint film, and consequently the pigment dispersing agent acts as aplasticizer in the paint film, which injuries the film performances suchas humidity resistance, water resistance, weather resistance and thelike and bleeds out from the surface of the paint film to badly affectthe gloss, hardness and adhesion property. Furthermore, thecompatibility with the binder resin having a high polarity reduces, sothat the pigment dispersing performances are degraded in these systems.On the other hand, when the hydroxyl value of the component B exceeds200, the polarity becomes excessively high and the water resistance andflexiblity of the paint film are injured, and also the compatibilitywith the binder resin having a low polarity reduces, so that theapplication thereof is restricted.

Moreover, in the component B having the glycidyl group, 1 mol ofhydroxyl group is produced from 1 mol of glycidyl group through thereaction with the component A, so that it is considered that 1 mol ofglycidyl group corresponds to 1 mol of hydroxyl group in the calculationof the hydroxyl value.

The component B contains one of glycidyl group, acetoacetoxy group andcyclocarbonate group as a reaction point to the component A at afunctional group number of 0.7-3.0 per molecule, preferably 1.0-2.0 permolecule. The term "molecule" used herein means a molecule having aweight average molecular weight by a gel permeation chromatography basedon polystyrene standard. When the functional group number of one ofglycidyl group, acetoacetoxy group and cyclocarbonate group is less than0.7 per molecule, a portion of the component B not reacting with thecomponent A becomes large and the pigment dispersing performances aredegraded, while when it exceeds 3.0, there is a possibility of promotingthe three-dimensional network structure through the reaction with thecomponent A and hence the increase of viscosity or gellation isundesirably caused.

Moreover, as an example, when the amount of the desirable functionalgroup is expressed by the term of equivalent value (epoxy equivalent),it corresponds substantially to a range of 1,000-200,000. Even in thecase of the functional group other than glycidyl group, if the desirableamount is expressed by the equivalent value, it is within the aboverange.

The component B contains one of glycidyl group, acetoacetoxy group andcyclocarbonate group in its side chain portion for the skeleton ofacrylic resin. Each of these functional groups in the component B reactswith the amino or imino group in the component A according to thefollowing reaction formula to form the pigment dispersing agentaccording to the invention.

(1) Reaction of Glycidyl Group ##STR5## (2l) Reaction of AcetoacetoxyGroup ##STR6## (3) Reaction of Cyclocarbonate Group ##STR7##

The introduction of these functional groups into the component B will bedescribed in detail below. For example, there are two methods, one ofwhich methods being a method of copolymerizing a monomer previouslyhaving the functional group with the other copolymerizable monomer andthe other of which methods being a method of previously forming acopolymer having no functional group and then introducing the functionalgroup thereinto. In the former method, use may be made of the followingmonomers.

The monomer containing glycidyl group includes, for example, glycidyl(metha)acrylate, allylglycidyl ether and the like. The monomercontaining acetoacetoxy group includes, for example, acetoacetoxyethyl(metha)acrylate, acetoacetoxypropyl (metha)acrylate, allylacetoacetateand the like. The monomer containing cyclocarbonate group includes, forexample, 4-(metha)acryloyloxymethyl-1,3-dioxolane-2-on,4-(metha)acryloyloxyethyl-1,3-dioxolane-2-on,4-(metha)acryloyloxypropyl-1,3-dioxolane-2-on,4-(metha)acryloyloxybutyl-1,3-dioxolane-2-on and the like.

As the monomer ingredient usually constituting the acrylic copolymer ofthe component B, there are mentioned various α, β- ethylenicallyunsaturated monomers always used in the art. For example, mention may bemade of alkyl esters of (metha)acrylic acid such as methyl(metha)acrylate, ethyl (metha)acrylate, propyl (metha)acrylate, butyl(metha)acrylate, octyl (metha)acrylate, lauryl (metha)acrylate, stearyl(metha)acrylate, cyclohexyl (metha)acrylate, phenyl (metha)acrylate,benzyl (metha)acrylate and the like; alkoxyalkyl esters such asmethoxyethyl (metha)acrylate, methoxybutyl (metha)acrylate, ethoxyethyl(metha)acrylate, ethoxybutyl (metha)acrylate and the like; hydroxyalkylesters such as 2-hydroxyethyl (metha)acrylate, 2-hydroxypropyl(metha)acrylate and the like; lactone-modified (metha)acrylates such asPlaccel FA-1, FA-2, FM-1, FM-2 and the like (trade name, made by DaicelChemical Industries Ltd.); di or monoalkyl esters of dibasic acids suchas maleic acid, fumaric acid and the like; acrylic acid, methacrylicacid, (metha)acrylonitrile, (metha)acrylamide, N-methylol(metha)acrylamide, N-methoxymethyl (metha)acrylamide, dimethylaminoethyl(metha)acrylate diethylaminoethyl (metha)acrylate, dimethylaminopropyl(metha)acrylate, styrene, α methyl styrene, vinyltoluene, vinyl acetate,vinyl chloride, various vinyl ethers, vinyl esters, allyl ethers, allylesters and so on.

The component C used in the second invention is a polyester resin havinga weight average molecular weight of 1,000-30,000 and containingisocyanate group or acetoacetoxy group in its terminal and has anyone ofthe following C₁ -C₆ structures.

    R.sub.1 --O--(CO--R.sub.2 --O).sub.n --CO--NH--R.sub.3 --NCO (C.sub.1)

    R.sub.1 --O--(CO--R.sub.2 --O).sub.n --CO--CH.sub.2 --CO--CH.sub.3 (C.sub.2)

    R.sub.1 --O--(CO--R.sub.4 --COO--CHR.sub.5 --CHR.sub.6 --O).sub.n --CO--NH--R.sub.3 --NCO                                   (C.sub.3)

    R.sub.1 --O--(CO--R.sub.4 --COO--CHR.sub.5 --CHR.sub.6 --O).sub.n --CO--CH.sub.2 --CO--CH.sub.3                             (C.sub.4)

    R.sub.1 --CO--()--CHR.sub.5 --CHR.sub.6 --O--COR.sub.4 --CO).sub.n --O --CHR.sub.5 --CHR.sub.6 --OCO--NH--R.sub.3 --NCO          (C.sub.5)

    R.sub.1 --CO--(O--CHR.sub.5 --CHR.sub.6 --O--COR.sub.4 --CO).sub.n --O --CHR.sub.5 --CHR.sub.6 --OCO--CH.sub.2 COCH.sub.3        (C.sub.6)

R₁ : aliphatic, alicyclic or aromatic hydrocarbon group having a carbonnumber of 1-18,

R₂ : alkylene group having a carbon number of 1-7,

R₃ : residual group of aliphatic, alicyclic or aromatic diisocyanatehaving a carbon number of 6-20,

R₄ : Residual group of aliphatic, alicyclic or aromatic acid anhydridehaving a carbon number of 2-20,

R₅, R₆ : hydrogen atom, aliphatic, alicyclic or aromatic hydrocarbongroup having a carbon number of 1-20, --CH₂ --O--R₁ group or --CH₂--OCO--R₁ group

n: an integer of 1 or more.

The component C is an ingredient necessary when the pigment dispersingagent according to the invention is applied to not only the acrylicresin paints but also the polyester resin paints. The polyesterstructure in the component C has a compatibility with the polyesterresin and exhibits excellent pigment dispersing performances.

When the weight average molecular weight of the component C is less than1,000, it is difficult to form the sufficient, sterically repulsivelayer and the sufficient compatibility with polyester resin in the paintcan not be ensured, and consequently good pigment dispersingperformances can not be obtained in the polyester resin paints. While,when the molecular weight of the component C exceeds 30,000, it isdifficult to produce the component C with a good reproducibility,resulting in the unsuitable use as an industrial material.

The production of the component C will be described in detail below. Itis obtained by ring-opening polymerization of lactones with monovalentalcohol as a reaction initiator (corresponding to components C₁ and C₂),or by successively ring-opening reaction between acid anhydride andepoxy compound with monovalent alcohol or monovalent carboxylic acid asa reaction initiator to obtain an oligomer containing a hydroxyl groupin its terminal and then reacting such a hydroxyl group withdiisocyanate compound, diketene or acetoacetic acid ester (correspondingto components C₃, C₄, C₅ and C₆).

R₁ in the components C₁, C₂, C₃ and C₄ is an aliphatic, alicyclic oraromatic hydrocarbon group having a carbon number of 1-18.

As a feed material for R₁, mention may be made of monovalent alcoholsrepresented by R₁ OH such as methanol, ethanol, propanol, butanol,pentanol, hexanol, heptanol, octanol, nonanol, decanol, lauryl alcohol,cetyl alcohol, oleyl alcohol, stearyl alcohol and various syntheticalcohols; alicyclic monovalent alcohols such as cyclopentanol,cyclohexanol and alkyl substituted compounds thereof; phenol, benzylalcohol, alkyl substituted compounds thereof and the like. Similarly,various glycol ethers, glycol esters and so on may be used.

R₂ in the components C₁ and C₂ is an alkylene group having a carbonnumber of 1-7. As a feed material for R₂, mention may be made oflactones such as ε-caprolactone, propiolactone, valerolactone and so on.

R₁ in the components C₅ and C₆ is the same as in the above R₁. In thiscase, monovalent carboxylic acids represented by R₁ COOH and obtained bysubstituting OH group of the monoalcohol R₁ OH in the above componentsC₁ -C₄ are mentioned, for example, as a feed material for this R₁.

R₄ in the components C₃, C₄, C₅ and C₆ is a residual group of aliphatic,alicyclic or aromatic acid anhydride having a carbon number of 2-20. Asa feed material for R₄, mention may be made of acid anhydridesrepresented by ##STR8## such as maleic anhydride, succinic anhydride,phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalicanhydride, tetrahalophthalic anhydride, hexahalophthalic anhydride,hymic anhydride, hetic anhydride, various alkyl or alkenylsuccinicanhydrides and the like.

R₅ and R₆ in the components C₃, C₄, C₅ and C₆ are a hydrogen atom or analkyl group having a carbon number of 1-20 or --CH₂ --O--R₁ or ##STR9##As a feed material for CHR₅ --CHR₆, mention may be made of epoxycompounds represented by ##STR10## such as olefin oxides having a carbonnumber of 2-20, styrene oxide, alkylglycidyl ethers or glycidyl estershaving a carbon number of 1-20, phenylglycidyl ether, alkyl-substitutedphenylglycidyl ether and the like.

R₃ in the components C₁, C₃ and C₅ is a residual group of aliphatic,alicyclic or aromatic diisocyanate having a carbon number of 6-20. As afeed material for R₃, mention may be made of diisocyanate compoundsrepresented by OCN--R--NCO such as tolylene diisocyanate, isophoronediisocyanate, 4,4'-diphenylmethane diisocyanate, hexamethylenediisocyanate, lysine diisocyanate, methylcyclohexane-2,4 (2,6)diisocyanate, 4,4'-methylenebis (cyclohexylisocyanate),1,3-(isocyanatemethyl) cyclohexane, trimethylhexamethylene diisocyanate,dimer acid diisocyanate and the like.

The pigment dispersing agent according to the first invention iscomprised of the component A₁ and the component B and is obtained byreacting the component A₁ with the component B at a mol ratio of A₁ to Bof 1:1-40. When the mol ratio is less than 1:1, the sterically repulsivelayer is not formed sufficiently and the pigment dispersing performancesare degraded, while when it exceeds 1:40, the desorption from thepigment surface is apt to be caused and the dispersibility is degraded.

The pigment dispersing agent according to the second invention iscomprised of the component A₂, the component B and the component C andis obtained by reacting the component A₂ with the components B and C ata mol ratio of A₂ :B:C of 1:1:1-1:40:40. When the mol ratio of A₂ :B:Cis less than 1:1:1, the sterically repulsive layer is not formedsufficiently and the good compatibility with various resins is notobtained, while when it exceeds 1:40:40, the desorption of thedispersing agent from the pigment surface is undesirably caused. In sucha three component system, the components A₂ and B are combined with oneof components C₁ -C₆ as the component C, but two or more components Cmay be applied without giving any further merit.

That is, the pigment dispersing agent according to the invention is acombination of the above-mentioned components and is desirable to havean amine value of 10-500 mg KOH/g as the agent itself. When the aminevalue is less than 10 mg KOH/g, the adsorbing force to the pigment islacking, while when it exceeds 500 mg KOH/g, the ratio of the stericallyrepulsive group to the adsorbing group is very small and the sufficientpigment dispersing performances may not be obtained.

Moreover, the measurement of amine value is carried out by using asolution of p-toluene sulfonic acid in acetic acid as a titrating agentin a solvent of acetic acid and calculating from an amount of p-toluenesulfonic acid required for neutralization through nonaqueouspotentiometric titration.

The production of the pigment dispersing agent according to theinvention will be described below.

(1) Production of Component B

The acrylic copolymer of the component B is produced by copolymerizingtwo or more α, β-ethylenically unsaturated monomers constituting thecomponent B as previously mentioned in the presence of a polymerizationinitiator. As the copolymerization method, well-known methods such assolution polymerization, block polymerization, suspension polymerizationand the like may be applied. Among them, solution polymerization methodis preferable.

As the polymerization initiator, use may be made of any substancesusually used in the vinyl-type polymerization, which includes, forexample, azobisisobutyronitrile, di-t-butyl peroxide, benzoylperoxide,t-butyl peroxybenzoate, t-butyl peroctoate, cumene hydroperoxide,lauroyl peroxide, acetyl peroxide, methylethyl ketone peroxide, dicumylperoxide and the like.

The organic solvent used in the solution polymerization is notparticularly critical. As the solvent, there may be used one or more ofaromatic hydrocarbons such as toluene, xylene, ethylbenzene, Solveso#100 and Solveso #150 (registered trade mark, made by Exxon ChemicalCo.), turpentine oil, tetraline and the like; aliphatic hydrocarbonssuch as n-hexane, cyclohexane, methyl cyclohexane, n-heptane, n-octane,n-decane, mineral spirit, isooctane, nonane, trimethylhexane, solventnaphtha, Isopar (registered trade mark, made by Exxon Chemical Co.),Newsol Delax (registered trade mark, made by Nippon Oil Co., Ltd.) andthe like; esters such as methyl acetate, ethyl acetate, n-butyl acetate,isobutyl acetate and the like; ethers such as ethyl ether,tetrahydrofuran, dioxane, diglyme and the like; ketones such as acetone,methyl ethyl ketone, methyl isobutyl ketone, methyl amyl ketone,cyclohexanone, isophorone and the like; alcohols such as methyl alcohol,ethyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol,methylisobutyl carbinol, cyclohexanol, benzyl alcohol and the like;cellosolves and esters thereof such as ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, ethylene glycol monobutyl ether,propylene glycol monomethyl ether, propylene glycol monoethyl ether,propylene glycol monobutyl ether and so on; chlorinated hydrocarbonssuch as methylene chloride, trichloroethylene, perchloroethylene,o-dichlorobenzene and the like; dimethylformamide, dimethylsulfoxide andso on.

(1)-a: Production of Glycidyl Group-Containing Acrylic Copolymer

The glycidyl group-containing monomer such as glycidyl (metha)acrylate,allylglycidyl ether or the like is copolymerized with the aforementionedusual α, β-ethylenically unsaturated monomer.

(1)-b: Production of Acetoacetoxy Group-Containing Acrylic Copolymer

The acetoacetoxy group-containing acrylic copolymers are produced byanyone of the following three methods.

In a first method, a monomer containing an acetoacetic acid ester groupsuch as acetoacetoxyethyl (metha)acrylate, acetoacetoxypropyl(metha)acrylate or the like is copolymerized with the above usual α,β-ethylenically unsaturated monomer.

In a second method, a hydroxyalkyl ester of (metha)acrylic acid such as2-hydroxyethyl (metha)acrylate, 2-hydroxypropyl (metha)acrylate or thelike is copolymerized with the above usual α, β-ethylenicallyunsaturated monomer to obtain an acrylic copolymer containing hydroxylgroup. Then, the reaction product is held at a temperature of 0°-150° C.and reacted with diketene for 1-8 hours to acetoacetylate a requiredamount of the hydroxyl group. In this case, a catalyst is notnecessarily used. If necessary, a slight amount of a tertiary amine suchas triethylamine or the like, or a carboxylate such as potassium acetateor the like, or an organic metal compound such as dibutyl tin dilaurateor the like is used as a catalyst.

In a third method, the same acrylic copolymer containing hydroxyl groupas in the second method is added with an alkyl acetoacetate such asmethyl acetoacetate, ethyl acetoacetate, propyl acetoacetate, butylacetoacetate, hexyl acetoacetate or the like, which is subjected to areaction for the removal of alcohol at 100°-200° C. for 1-8 hours, ifnecessary, in the presence of an ester exchange catalyst such as calciumacetate, lead oxide or the like.

(1)-c: Production of Cyclocarbonate Group-Containing Acrylic Copolymer

The cyclocarbonate group-containing acrylic copolymers are produced byeither of the following two methods. In a first method, α,β-ethylenically unsaturated monomer containing cyclocarbonate group suchas 4-(metha)acryloyloxymethyl-1,3-dioxolane-2-on,4-(metha)acryloyloxypropyl-1,3-dioxolane-2-on,4-(metha)acryloyloxybutyl-1,3-dioxolane-2-on,4-(metha)acryloyloxybutyl-1,3-dioxolane-2-on or the like iscopolymerized with the aforementioned usual α, β-ethylenicallyunsaturated monomer. Moreover, the cyclocarbonate group-containingmonomer can easily be obtained reacting α, β-ethylenically unsaturatedmonomer containing oxylane group (epoxy group) such as2-(metha)acryloyloxymethyl oxylane, 2-(metha)acryloyloxy-ethyl oxylane,2-(metha)acryloyloxypropyl oxylane, 2-(metha)acryloyloxybutyl oxylane orthe like with carbon dioxide gas in the presence of potassium iodide orsodium iodide and triphenylphosphine or quartenary ammonium salt as acatalyst at 40°-180° C. as described in DE-OS 3 529 263.

In a second method, the aforementioned oxylane group-containing monomeris previously copolymerized with the usual α, β-ethylenicallyunsaturated monomer and thereafter reacted with carbon dioxide gas as inthe first method to convert the oxylane group into cyclocarbonate group.

(2) Production of Component C (2)-a: Production of Components C₁ and C₂

An alcohol of R₁ OH and a lactone of ##STR11## are reacted in thepresence of a tertiary amine such as triethylamine or the like, or anorganic metal compound such as tetrabutoxy titanate or the like, or aphosphorus compound such as triphenylphosphine or the like as a catalystat 100°-200° C. for 1-10 hours to obtain a polyester oligomer containinghydroxyl group in its terminal. If the viscosity of the resultingproduct is high, the reaction may be carried out in the coexistence ofan organic solvent having no active hydrogen, if necessary.

The component C₁ is produced by reacting the above polyester oligomerwith a diisocyanate compound of OCN--R₃ --NCO in the absence or presenceof an organic metal compound such as dibutyltin dilaurate, a carboxylatesuch as potassium benzoate or a tertiary amine such as triethylenediamine or the like as a catalyst in such a manner that a mol ratio ofhydroxyl group of the above oligomer to the diisocyanate OCN--R₃ --NCOis within a range of 1:0.8-1:1.5, preferably 1:1. The reactionconditions are desirably 20°-80° C. and 1-10 hours.

The component C₂ is produced by reacting the above polyester oligomerwith diketene at a mol ratio of (diketene to hydroxyl group of0.9-1.1:1, preferably 1:1 under the same reaction conditions as in theabove item (1)-b. Alternatively, it may be produced by using acetoaceticacid ester instead of diketene through the reaction for the removal ofalcohol.

(2)-b: Production of Components C₃, C₄, C₅ and C₆

The components C₃ and C₄ are produced by reacting monovalent alcohol ofR₁ OH, acid anhydride of ##STR12## and epoxy compound of ##STR13## inthe absence or presence of a tertiary amine such as triethylene diamine,quaternary ammonium salt such as tetramethyl ammonium chloride, organiccarboxylate such as potassium benzoate or inorganic salt such aspotassium iodide as a catalyst at 100°-180° C. for 1-10 hours to obtaina polyester oligomer containing hydroxyl group in its terminal throughsuccessive ring-opening of the acid anhydride and epoxy compound. On theother hand, the components C₅ and C₆ are produced by reacting carboxylicacid of R₁ COOH instead of R₁ OH with the acid anhydride and epoxycompound under the same conditions as described above to obtain apolyester oligomer containing hydroxyl group in its terminal throughsuccessive ring-opening of the epoxy compound and acid anhydride.Moreover, if the viscosity of the resulting product during thesereactions is high, the reaction may be carried out in the co-existenceof an organic solvent containing no active hydrogen, if necessary. Inthe components C₃ and C₅, the above prepolymer is reacted withdiisocyanate compound in the same manner as in the component C₁, whilein the components C₄ and C₆, the prepolymer is reacted With diketene oracetoacetic acid ester in the same manner as in the component C₂,whereby the objective polyester compound containing isocyanate group oracetoacetoxy group in its terminal is obtained.

(3) Production of Pigment Dispersing Agent From Components A₁ and B

The pigment dispersing agent according to the first invention isproduced by mixing the components A₁ and B and then reacting them in theabsence of a catalyst for about 1-10 hours. The reaction temperature isdesirable to be 20°-140° C. in case of glycidyl group as a reactionpoint of the component B, 20°-100° C. in case of acetoacetoxy group and20°-120° C. in case of cyclocarbonate group. If it is required to use asynthetic solvent, anyone of the solvents described in the production ofthe component B is used.

(4) Production of Pigment Dispersing Agent From Components A₂, B and C

The pigment dispersing agent according to the second invention isproduced by mixing the components A₂, B and C and then reacting them inthe absence of a catalyst at 20°-100° C. for 1-10 hours. Alternatively,there are a method wherein the component A₂ is reacted with thecomponent B and then the component C is added thereto, and a methodwherein the component A₂ is reacted with the component C and then thecomponent B is added thereto. When the component A₂ is first reactedwith the component B, the reaction condition is the same as in the aboveitem (3), and the second reaction stage may only be carried out at20°-100° C. When the component A₂ is first reacted with the component C,it is desirable that the reaction is carried out 20°-100° C. at eachstage.

The pigment dispersing agents according to the invention are used forpaints, inks, toners and magnetic tape coating materials as well asvarious colorants. As an objective pigment, mention may be made ofinorganic pigments such as titanium dioxide, zinc oxide, cadmiumsulfide, iron oxide, calcium carbonate, red lead, zinc sulfide, bariumsulfate, barium carbonate, clay, talc, chrome yellow, carbon black andso on; organic pigments such as azo series, diazo series, condenseddiazo series, thioindigo series, indanthrone series, anthraquinoneseries, benzimidazolone series, phthalocyanine series, pyranthroneseries, anthrapyridine series, isoindolinone series, perylene series,quinacridone series, furavanthrone series, dioxazine series, piranthroneseries, perinone series and the like. The pigment dispersing agentsaccording to the invention exhibit an effect of enhancing the pigmentdispersibility against these pigments.

The pigment dispersing agent according to the invention is used in anamount as a solid content of 1-200% by weight, preferably 5-100% byweight to the pigment in a so-called pigment dispersion basecomposition. The pigment dispersion base composition is comprised of thepigment dispersing agent according to the invention, the pigment and theorganic solvent, or may further contain a part or whole of afilm-forming resin. Such a pigment dispersion base is dispersed by meansof a dispersing machine usually used in the art, such as roll mill, ballmill, sand grind mill, attritor, paint shaker, kneader, high speeddispersing machine, ultrasonic dispersing machine, dissolver or thelike, which is supplied for use in the colorant.

The paints obtained by using the pigment dispersing agent according tothe invention are excellent in the dispersibility of pigment and colorstrength and form a paint film having good gloss, distinctness of imageand smoothness. Furthermore, the pigment dispersing agent according tothe invention strongly adsorbs on the surface of the pigment to preventa tendency of agglomerating the pigment particles, resulting in theproduction of paints having an excellent storage stability and a highsolid content.

Moreover, the pigment dispersing agent according to the invention has acrosslinking point in the structure, so that it causes a curing reactionwith a crosslinking agent, and consequently the pigment dispersing agentis chemically fixed in the paint film likewise the case of thefilm-forming resin to chemically strengthen the boundary face betweenthe pigment and the resin. Therefore, there is no damage on the waterresistance, humidity resistance, weather resistance and the like of thepaint film. Furthermore, there is no bleeding of the dispersing agent onthe surface of the paint film, so that there is no reduction of gloss,surface hardness and the like and no degradation of adhesion propertybetween paint films. In addition, the invention solves the difficultyusing the polymer type pigment dispersing agent. That is, the pigmentdispersing agents according to the invention can be applied to both theacrylic resin paint and polyester resin paint greatly used in the art,and also are applicable to paint formulations containing resins of lowor high polarity.

The following examples are given in illustration of the invention andare not intended a limitations thereof. In these examples, "part" and"%" are by weight.

SYNTHESIS EXAMPLES 1 AND 2 <Production of Polyester Resin>

A polyester resin as a main film-forming component for polyester resinseries paint was produced as follows.

Into a reaction vessel provided with a reflux condenser, an inlet tubefor nitrogen gas, a thermometer and a stirring blade were chargedstarting materials having a composition (Synthesis Examples 1 and 2) asshown in the following Table 1, which were heated to an upper limittemperature of 230° C. under a stream of nitrogen gas with stirring.Water generated in the progress of the reaction was removed togetherwith xylene through azeotropic distillation and the heating wascontinued till the acid value was about 10 to complete the reaction. Theresulting resin was diluted with xylene so as to render the nonvolatilecontent into 60%, whereby the objective polyester resins PE-1 and PE-2were obtained.

                  TABLE 1                                                         ______________________________________                                                         Synthesis Example                                                               1        2                                                 Polyester resin No.                                                                              PE-1     PE-2                                              ______________________________________                                        lauric acid        4.5      --                                                tall oil fatty acid                                                                              --       16.2                                              castor oil         --        3.8                                              phthalic anhydride 5.8      17.7                                              isophthalic acid   21.8     --                                                adipic acid        1.6       5.0                                              neopentyl glycol   12.8     10.4                                              trimethylol propane                                                                              7.4      --                                                pentaerythritol    --        8.6                                              Cardula E-10.sup.1)                                                                              8.3      --                                                xylene             1.8      --                                                xylene (diluting solvent)                                                                        36.0     38.3                                              nonvolatile content (%)                                                                          60       60                                                resin acid value   10       10                                                ______________________________________                                         .sup.1) Cardula E10: trade name, made by Shell Chemicals Co., Ltd.            (glycidylester of versatic acid)                                         

SYNTHESIS EXAMPLES 3-11 <Production of Acrylic Resin>

An acrylic resin as a main film-forming component for acrylic resinseries paints was produced as follows.

Into a reaction vessel provided with a reflux condenser, an inlet tubefor nitrogen gas, a thermometer, a stirring blade and a monomer droppingdevice was charged a solvent shown in the following Table 2 and then thetemperature was raised to a reflux temperature under a stream ofnitrogen gas. A mixture of each monomer and t-butylperoxy benzoate as apolymerization initiator as shown in Table 2 was added dropwise throughthe dropping device over 2 hours under reflux state. After the addition,the stirring was further continued for 5 hours under reflux state tocomplete the polymerization, whereby the objective varnishes AC-1-9AC-9were obtained.

SYNTHESIS EXAMPLES 12-18

A polyester resin (component C) for the pigment dispersing agent wasproduced as follows.

Into a reaction vessel provided with a reflux condenser, an inlet tubefor nitrogen gas, a dropping funnel, a thermometer and a stirring bladewere charged xylene as a solvent, tetrabutoxy titanate and 2-ethylhexanol or decanol among ingredients shown in the following Table 3 andthen the temperature was raised to 130°-140° C. under a stream ofnitrogen gas. Further, ε-caprolactone shown in Table 3 wa added dropwisethrough the dropping funnel over 2 hours under reflux state andthereafter the stirring wa continued for about 5 hours.

In Synthesis Example 12, the temperature of the reaction product waslowered to 30° C. and tolylene diisocyanate was added in an amount shownin Table 3 and then the stirring was continued for about 2 hours toobtain a polyester resin C₁ having properties shown in Table 3 andcontaining isocyanate group in its terminal.

In Synthesis Examples 13-18, the temperature of the reaction product waslowered to 70° C. and triethylene diamine shown in Table 3 was added andthen diketene shown in Table 3 was added dropwise over about 2 hourswith strong stirring to produce polyester resins C₂ -1-C₂ -6 containingacetoacetoxy group in their terminal.

SYNTHESIS EXAMPLES 19-22

In the same synthesis vessel as in Synthesis Example 12, toluene as asolvent, any one of lauric acid, octylic acid, decanol and cetylalcohol, phthalic anhydride and tetramethyl ammonium chloride as shownin Table 3 were mixed and then rendered into a reflux state of about135° C. Next, butylglycidyl ether or a mixture of butylglycidyl etherand phenylglycidyl ether in Table 3 was added dropwise through thedropping funnel over about 1 hour, which was maintained under refluxstate for about 5 hours. After the completion of the reaction, xylene inTable 3 was added to conduct dilution.

In Synthesis Examples 19 and 21, the temperature of the reaction productwas lowered to 30° C., and dibutyltin dilaurate and tolylenediisocyanate in Table 3 were added and then the stirring was continuedfor about 2 hours to complete the reaction.

In Synthesis Examples 20 and 22, the temperature of the reaction productwas lowered to about 50° C., and triethylene diamine in Table 3 wasadded and further diketene was added dropwise through the droppingfunnel over about 30 minutes with strong stirring and the stirring wasfurther continued for 4 hours to produce polyester resins.

SYNTHESIS EXAMPLES 23-72

A mixture of monomers as shown in the following Table 4 was addeddropwise through the dropping funnel in the same vessel according to thesame method as described in Synthesis Examples 3-11 over about 2 hours.After the addition, the stirring was further continued for 2 hours toobtain acrylic resins (B₁ -1-B₁ -10, B₂ -1 -B₂ -25, B₃ -1 -B3-15) as acomponent B for pigment dispersing agent.

Moreover, in Synthesis Examples 51 and 52, the reaction mixture afterthe completion of the above reaction was cooled to about 50° C, andtriethylene diamine in Table 4 was added and then diketene in Table 4was added dropwise over about 30 minutes with strong stirring and thestirring was further continued for about 4 hours to complete theproduction.

EXAMPLES 1-26

Pigment dispersing agents of A₁ -B type were produced according to acomposition ratio as shown in the following Table 5 as follows.

Into the same vessel as in Synthesis Example 1 was charged a component Bor a mixture of component B and solvent as shown in Table 5, and then acomponent A₁ was added with strong stirring, which were heated to atemperature shown in the column for reaction conditions of Table 5 andreacted at this temperature for a time shown in the column for reactionconditions of Table 5 to produce the objective pigment dispersingagents.

Moreover, the combination of components A₁ and B is represented, forexample, as A₁ -B₁ in the column for structure of pigment dispersingagent of Table 5, wherein B₁ is component B containing gylcidyl group,B₂ is component B containing acetoacetoxy group and B₃ is component Bcontaining cyclocarbonate group.

EXAMPLES 27-53

Pigment dispersing agents of A₂ -B-C type were produced according to acomposition ratio as shown in the following Table 6 as follows.

Into the same vessel as in Synthesis Example 1 was charged a mixture ofcomponent B and solvent as shown in Table 6, and then a component A₂ wasadded at room temperature with strong stirring, which were heated andreacted under synthesis conditions shown in the column for reactionconditions in A₂ -B reaction of Table 6 likewise Examples 1-26. Then,the temperature of the reaction product was adjusted to a temperatureshown in the column of A₂ -C reaction conditions and a component C wasadded dropwise over about 30 minutes and stirred for a time described inthe same column to produce the objective pigment dispersing agents.

Moreover, the combination of components A₂, B and C is represented, forexample, as A₂ -B₁ -C₁ in the column for structure of pigment dispersingagent of Table 6, wherein B₁ -B₃ and C₁ -C₆ are the same components aspreviously mentioned.

APPLICATION EXAMPLES 1-64

Dispersion pastes and paints each having a composition as shown in thefollowing Table 7 were prepared by using the pigment dispersing agentsshown in Tables 5 and 6, and then the properties of the paste and filmperformances of the paint were measured to evaluate the effect of thepigment dispersing agent according to the invention.

That is, starting materials were uniformly mixed in accordance with aformulation of dispersion paste shown in Table 7, and then the mixturewas dispersed by means of a paint shaker (made by Red Devil Co.) toobtain a dispersion paste. The viscosity and storage stability of thisdispersion paste are shown in the column of paste properties of Table 7.

Then, starting materials using the above dispersion paste were mixed inaccordance with a formulation for paint shown in Table 7 and thoroughlystirred to prepare a paint. To this paint was added a thinner fordilution (cellosolve acetate/ xylene=50/50 mixed solvent) so as toadjust a viscosity to 20 seconds (25° C.) through Ford Cup No. 4,whereby a finishing paint for spray coating was obtained.

Next, a primer coated plate was provided in order to evaluate the filmperformances of this paint. That is, an SPCC dull steel sheet (size:0.8×100×150 mm) subjected to a zinc phosphate treatment was subjected toan electrodeposition with a general-purpose black cation electropaint(Aqua No. 4200, trade name, made by Nippon Oil and Fats Co., Ltd.) andthen baked at 170° C. for 30 minutes to obtain a dried paint film of 20μm in thickness. Thereafter, an alkyd/melamine series gray intermediatepaint for automotive (Epico No. 1500 sealer, trade name, made by NipponOil and Fats Co., Ltd.) was diluted with a thinner (Thinner TR 101,trade name, made by Nippon Oil and Fats Co., Ltd.) so as to adjust aviscosity to 30 seconds (25° C.) through Ford Cup No. 4 and then sprayedonto the above primer coated sheet and baked at 140° C. for 30 minutesto obtain a dried paint film of 40 μm in thickness. Then, theaforementioned finishing paint was sprayed onto the thus painted steelsheet and baked at 140° C. for 30 minutes to obtain a test film(finished film thickness: 40 μm). The specular gloss at 30° (Drigongoniophotometer, made by Hunter Laboratories), humidity resistance,weather resistance and presence or absence of bleeding phenomenon ofdispersing agent onto film surface were evaluated with respect to thethus obtained test specimen. The result are also shown in Table 7.

As seen from Table 7, all of the dispersion pastes using the pigmentdispersing agent according to the invention are excellent in the storagestability. As to the film performances, it has been confirmed that thegloss is excellent in all paint films and the humidity resistance andweather resistance are not damaged. Furthermore, there is observed nobleeding of the pigment dispersing agent on the film surface.

COMPARATIVE EXAMPLES 1-13

Pigment dispersing agents of Comparative Examples 1-13 were produced inaccordance with a composition ratio a shown in the following Table 8 inA-B system in the same manner as in Examples 1-26 and in A-B-C system inthe same manner as in Examples 27-53.

APPLICATION COMPARATIVE EXAMPLES 1-16

Dispersion pastes and paints as shown in the following Table 9 wereproduced by using the pigment dispersing agents of Comparative Examples1-13 and the pigment dispersing agents of Examples 2 and 22. Either ofstorage stability of dispersion paste and film performances of paint asshown in Table 9 is poorer than that shown in Table 7.

                                      TABLE 2                                     __________________________________________________________________________                        Synthesis Example                                                             3     4     5     6     7                                 __________________________________________________________________________    Acrylic resin No.   AC-1  AC-2  AC-3  AC-4  AC-5                              Solvent                                                                             xylene        40    40    40    10    20                                      isobutyl acetate                                                                            --    --    --    30    20                                Monomer                                                                             methyl methacrylate                                                                           23.4                                                                                15.0                                                                                30.5                                                                                32.0                                                                                28.0                            composi-                                                                            ethyl acrylate                                                                              --      22.0                                                                              --    --    --                                tion  butyl acrylate                                                                                13.3                                                                              --      20.0                                                                              --      5.0                                   butyl methacrylate                                                                          --    --    --      5.0   5.0                                   hexyl methacrylate                                                                            10.0                                                                              --    --    --    --                                      lauryl methacrylate                                                                         --      10.0                                                                              --    --      12.0                                  styrene       --      5.0 --      13.0                                                                                4.0                                   2-hydroxyethyl acrylate                                                                     --      7.0 --      8.0   5.0                                   2-hydroxyethyl methacrylate                                                                   12.0                                                                              --      8.0 --    --                                      acrylic acid    0.7   0.5   1.0 --    --                                      t-butyl peroxy benzoate                                                                       0.6   0.5   0.5   2.0   1.0                             Properties                                                                          nonvolatile content (%)                                                                     60    60    60    60    60                                      weight average molecular                                                                    21,000                                                                              24,000                                                                              25,200                                                                              33,800                                                                              58,500                                  weight                                                                        hydroxyl value                                                                              86    56    58    64    40                                __________________________________________________________________________                          Synthesis Example                                                             8      9      10     11                                 __________________________________________________________________________    Acrylic resin No.     AC-6   AC-7   AC-8   AC-9                               Solvent                                                                              xylene         25     20     52       39.8                                    isobutyl acetate                                                                             15     20     --     --                                 Monomer                                                                              methyl methacrylate                                                                            2.0    30.0   16.4   24.7                             composi-                                                                             ethyl acrylate --     --     --     --                                 tion   butyl acrylate   5.0    5.0    15.8 --                                        butyl methacrylate                                                                             10.0   4.0  --       16.9                                    hexyl methacrylate                                                                           --     --     --     --                                        lauryl methacrylate                                                                            6.0    3.0  --     --                                        styrene          30.0    11.0                                                                                5.2    5.0                                     2-hydroxyethyl acrylate                                                                        5.0    5.0  --     --                                        2-hydroxyethyl methacrylate                                                                  --     --       9.7    11.9                                    acrylic acid   --     --       0.3    1.1                                     t-butyl peroxy benzoate                                                                        2.0    2.0    0.6    0.6                              Properties                                                                           nonvolatile content (%)                                                                      60     60     50     60                                        weight average molecular                                                                     28,200 29,300 20,000 21,000                                    weight                                                                        hydroxyl value 40     40     80     86                                 __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________                          Synthesis Example                                                             12   13   14   15   16   17                             __________________________________________________________________________    Polyester resin No.   C.sub.1                                                                            C.sub.2 -1                                                                         C.sub.2 -2                                                                         C.sub.2 -3                                                                         C.sub.2 -4                                                                         C.sub.2 -5                     Solvent                                                                             xylene          40   40   40   40   40   40                                   toluene         --   --   --   --   --   --                             Monomer                                                                             ε-caprolactone                                                                          55.08                                                                              58.44                                                                              49.17                                                                              53.47                                                                              57.11                                                                              58.81                        composi-                                                                            lauric acid     --   --   --   --   --   --                             tion  octylic acid    --   --   --   --   --   --                                   phthalic anhydride                                                                            --   --   --   --   --   --                                   2-ethyl hexanol   2.1                                                                                 0.92                                                                              6.5                                                                              --   --   --                                   decanol         --   --   --      4.21                                                                               1.85                                                                              0.7                                cetyl alcohol   --   --   --   --   --   --                                   butyl glycidyl ether                                                                          --   --   --   --   --   --                                   phenyl glycidyl ether                                                                         --   --   --   --   --   --                                   tetrabutoxy titanate                                                                             0.02                                                                               0.02                                                                               0.02                                                                               0.02                                                                               0.02                                                                               0.02                              tetramethyl ammonium chloride                                                                 --   --   --   --   --   --                                   triethylene diamine                                                                           --      0.01                                                                               0.01                                                                               0.01                                                                               0.01                                                                               0.01                              dibutyltin dilaurate                                                                          --   --   --   --   --   --                                   tolylene diisocyanate                                                                           2.8                                                                              --   --   --   --   --                                   diketene        --      0.61                                                                              4.3                                                                                 2.29                                                                               1.01                                                                               0.46                        Properties                                                                          nonvolatile content (%)                                                                       60   60   60   60   60   60                                   weight average molecular                                                                      3,700                                                                              8,500                                                                              1,200                                                                              2,250                                                                              5,120                                                                              11,200                               weight                                                                  __________________________________________________________________________                          Synthesis Example                                                             18    19    20    21    22                              __________________________________________________________________________    Polyester resin No.   C.sub.2 -6                                                                          C.sub.3                                                                             C.sub.4                                                                             C.sub.5                                                                             C.sub.6                         Solvent                                                                             xylene          40    25    25    25    25                                    toluene         --    15    15    15    15                              Monomer                                                                             ε-caprolactone                                                                          41.67                                                                             --    --    --    --                              composi-                                                                            lauric acid     --    --    --      2.5 --                              tion  octylic acid    --    --    --    --      2.9                                 phthalic anhydride                                                                            --      27.5                                                                                29.4                                                                                28.5                                                                                26.9                                2-ethyl hexanol --    --    --    --    --                                    decanol           11.85                                                                               3.6 --    --    --                                    cetyl alcohol   --    --      2.4 --    --                                    butyl glycidyl ether                                                                          --      21.2                                                                                18.2                                                                                26.7                                                                                13.2                                phenyl glycidyl ether                                                                         --      3.5    9.07                                                                             --      15.2                                tetrabutoxy titanate                                                                             0.02                                                                             --    --    --    --                                    tetramethyl ammonium chloride                                                                 --       0.06                                                                                0.06                                                                                 0.06                                                                               0.06                               triethylene diamine                                                                              0.01                                                                             --       0.01                                                                             --       0.01                               dibutyltin dilaurate                                                                          --       0.04                                                                             --       0.04                                                                             --                                    tolylene diisocyanate                                                                         --      4.1 --      2.2 --                                    diketene           6.45                                                                             --       0.86                                                                             --       1.73                         Properties                                                                          nonvolatile content (%)                                                                       60    60    60    60    60                                    weight average molecular                                                                      800   2,580 6,000 4,670 2,960                                 weight                                                                  __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________                           Synthesis Example                                                             23  24   25   26   27                                  __________________________________________________________________________    Acrylic resin No.      B.sub.1 -1                                                                        B.sub.1 -2                                                                         B.sub.1 -3                                                                         B.sub.1 -4                                                                         B.sub.1 -5                          Solvent                                                                             xylene           40  40   40   10.5 20.5                                      isobutyl acetate --  --   --   26.2 15.4                                      ethyl acetate    --  --   --    5.19                                                                               5.23                               Monomer                                                                             methyl methacrylate                                                                            30.0                                                                              14.15                                                                              33.03                                                                              31.4 25.6                                composi-                                                                            ethyl acrylate   --  12.0 --   --   --                                  tion  butyl acrylate   10.0                                                                              --   22.1 --    5.1                                      butyl methacrylate                                                                             --  --   --    4.2  5.1                                      hexyl methacrylate                                                                             10.0                                                                              --   --   --   --                                        lauryl methacrylate                                                                            --  12   --   --   12.3                                      styrene          --  9.9  --   12.6  4.1                                      2-hydroxyethyl acrylate                                                                        --  --   --    9.1  6.0                                      2-hydroxyethyl methacrylate                                                                     3.7                                                                              8.9  3.8  --   --                                        glycidyl acrylate                                                                              --  --   --   --   --                                        glycidyl methacrylate                                                                           2.0                                                                               0.85                                                                               0.37                                                                               0.18                                                                               0.16                                     t-butyl peroxy benzoate                                                                         4.3                                                                              2.2  0.7   0.63                                                                               0.51                               Properties                                                                          nonvolatile content (%)                                                                        60  60   60   58.1 58.9                                      hydroxyl value   40  70   30   77   50                                        weight average molecular weight                                                                5,000                                                                             10,000                                                                             25,000                                                                             80,000                                                                             90,000                                    number of epoxy group in one molecule                                                           1.2                                                                              1.0  1.1   1.7  1.7                                      number of acetoacetoxy group in                                                                --  --   --   --   --                                        one molecule                                                                  number of cyclocarbonate group in                                                              --  --   --   --   --                                        one molecule                                                            __________________________________________________________________________                          Synthesis Example                                                             28   29   30   31   32                                  __________________________________________________________________________    Acrylic resin No.     B.sub.1 -6                                                                         B.sub.1 -7                                                                         B.sub.1 -8                                                                         B.sub.1 -9                                                                         B.sub.1 -10                         Solvent                                                                             xylene          26.0 15.3 40   40   60                                        isobutyl acetate                                                                              10.4 20.4 --   --   --                                        ethyl acetate    5.34                                                                               5.08                                                                              --   --   --                                  Monomer                                                                             methyl methacrylate                                                                            1.8 30.6 33.23                                                                              31.9 22.61                               composi-                                                                            ethyl acrylate  --   --   --   --   --                                  tion  butyl acrylate   5.2  5.1 22.1 22.1 14.7                                      butyl methacrylate                                                                            10.4  4.1 --   --   --                                        hexyl methacrylate                                                                            --    --  --   --   --                                        lauryl methacrylate                                                                            6.2  3.0 --   --   --                                        styrene         31.3 12.2 --   --   --                                        2-hydroxyethyl acrylate                                                                        2.1  3.1 --   --   --                                        2-hydroxyethyl methacrylate                                                                   --   --   3.8  3.8  2.5                                       glycidyl acrylate                                                                              0.26                                                                               0.20                                                                              --   --   --                                        glycidyl methacrylate                                                                         --   --    0.17                                                                              1.5   0.06                                     t-butyl peroxy benzoate                                                                        1.0  0.92                                                                              0.7  0.7   0.13                               Properties                                                                          nonvolatile content (%)                                                                       58.3 59.2 60   60   40                                        hydroxyl value  19   27   30   37   30                                        weight average molecular weight                                                               30,000                                                                             40,000                                                                             25,200                                                                             25,000                                                                             110,000                                   number of epoxy group in one molecule                                                          1.0  1.0 0.5  4.4  1.1                                       number of acetoacetoxy group in                                                               --   --   --   --   --                                        one molecule                                                                  number of cyclocarbonate group in                                                             --   --   --   --   --                                        one molecule                                                            __________________________________________________________________________                          Synthesis Example                                                             33  34  35  36  37  38                                  __________________________________________________________________________    Acrylic resin No.     B.sub.2 -1                                                                        B.sub.2 -2                                                                        B.sub.2 -3                                                                        B.sub.2 -4                                                                        B.sub.2 -5                                                                        B.sub.2 -6                          Solvent                                                                             xylene          51.58                                                                             49.72                                                                             50.11                                                                             50.21                                                                             50.23                                                                             52.49                                     isobutyl acetate                                                                              --  --  --  --  --  --                                        ethyl acetate   --  --  --  --  --  --                                  Monomer                                                                             methyl acrylate --  --  10.2                                                                              --  --  --                                  compo-                                                                              methyl methacrylate                                                                           12.5                                                                              15.1                                                                              --  20.4                                                                              20.3                                                                              21.1                                sition                                                                              ethyl acrylate  --  2.6 --  --  --  --                                        ethyl methacrylate                                                                            --  --  10.2                                                                              --  9.9 --                                        propyl methacrylate                                                                           --  --  15.7                                                                              --  --  12.0                                      butyl acrylate  10.4                                                                              15.1                                                                              10.2                                                                              15.3                                                                              15.2                                                                              10.5                                      butyl methacrylate                                                                            10.4                                                                              15.1                                                                              --  --  --  --                                        hexyl methacrylate                                                                            --  --  --  9.4 --  --                                        styrene         8.3 --  --  --  --  --                                        2-hydroxyethyl methacrylate                                                                   5.5 1.1 2.3 3.4 3.4 3.3                                       acetoacetoxyethyl methacrylate                                                                 0.62                                                                              0.63                                                                              0.63                                                                              0.63                                                                              0.51                                                                              0.35                                     t-butyl peroxy benzoate                                                                       0.7  0.65                                                                              0.66                                                                              0.66                                                                              0.46                                                                              0.26                               Properties                                                                          nonvolatile content (%)                                                                       47.7                                                                              49.7                                                                              49.2                                                                              49.1                                                                              49.3                                                                              48.2                                      hydroxyl value  50  10  20  30  30  30                                        weight average molecular                                                                      19,500                                                                            21,050                                                                            19,800                                                                            20,100                                                                            24,900                                                                            35,700                                    weight                                                                        number of epoxy group in one                                                                  --  --  --  --  --  --                                        molecule                                                                      number of acetoacetoxy group                                                                  1.2 1.2 1.2 1.2 1.2 1.2                                       in one molecule                                                               number of cyclocarbonate                                                                      --  --  --  --  --  --                                        group in one molecule                                                   __________________________________________________________________________                          Synthesis Example                                                             39 40  41 42  43 44  45                                 __________________________________________________________________________    Acrylic resin No.     B.sub.2 -7                                                                       B.sub.2 -8                                                                        B.sub.2 -9                                                                       B.sub.2 -10                                                                       B.sub.2 -11                                                                      B.sub.2 -12                                                                       B.sub.2 -13                        Solvent                                                                             xylene          48.2                                                                             49.62                                                                             48.7                                                                             40.5                                                                              45.8                                                                             44.6                                                                              44.5                                     isobutyl acetate                                                                              -- --  -- --  -- 5   5                                        ethyl acetate   -- --  -- --  -- --  --                                 Monomer                                                                             methyl acrylate -- --  -- --  -- --  --                                 compo-                                                                              methyl methacrylate                                                                           20.0                                                                             20.1                                                                              20.4                                                                             20.3                                                                              -- 22.8                                                                              --                                 sition                                                                              ethyl acrylate  -- --  -- --  21.4                                                                             --  18.1                                     ethyl methacrylate                                                                            -- --  -- --  -- --  --                                       propyl methacrylate                                                                           -- --  -- --  -- --  --                                       butyl acrylate  15.0                                                                             15.1                                                                              15.3                                                                             20.3                                                                              -- 18  --                                       butyl methacrylate                                                                            -- --  -- 11.1                                                                              14.1                                                                              3.57                                                                             15                                       hexyl methacrylate                                                                            9.1                                                                              9.4 -- --  5.0                                                                              --  --                                       styrene         -- --  6.8                                                                              --  -- --  10                                       2-hydroxyethyl methacrylate                                                                   4.6                                                                              4.6 5.7                                                                              6.9 7.0                                                                              5.2 6.1                                      acetoacetoxyethyl methacrylate                                                                1.1                                                                               0.53                                                                             1.1                                                                              0.9 1.6                                                                               0.43                                                                             0.6                                      t-butyl peroxy benzoate                                                                       2.0                                                                               0.65                                                                             2.0                                                                              1.2 4.9                                                                              0.4 0.5                                Properties                                                                          nonvolatile content (%)                                                                       49.8                                                                             49.8                                                                              49.2                                                                             59.5                                                                              49.1                                                                             50  50                                       hydroxyl value  40 40  50 50  62 45  55                                       weight average molecular                                                                      9,820                                                                            19,900                                                                            9,800                                                                            14,000                                                                            5,300                                                                            26,100                                                                            20,500                                   weight                                                                        number of epoxy group in one                                                                  -- --  -- --  -- --  --                                       molecule                                                                      number of acetoacetoxy group                                                                  1.0                                                                              1.0 1.0                                                                              1.0 0.8                                                                              1.0 1.2                                      in one molecule                                                               number of cyclocarbonate                                                                      -- --  -- --  -- --  --                                       group in one molecule                                                   __________________________________________________________________________                          Synthesis Example                                                             46  47  48  49  50  51                                  __________________________________________________________________________    Acrylic resin No.     B.sub.2 -14                                                                       B.sub.2 -15                                                                       B.sub.2 -16                                                                       B.sub.2 -17                                                                       B.sub.2 -18                                                                       B.sub.2 -19                         Solvent                                                                             xylene          30  20  30  30  30  35                                        isobutyl acetate                                                                              --  --  --  --  --  --                                        ethyl acetate   --  --  --  --  --  --                                        toluene         10  10  10  10   5  5                                         Solveso #150    --  10  --  --   5  --                                  Monomer                                                                             methyl methacrylate                                                                           30  20  --  19  11  --                                  composi-                                                                            ethyl acrylate  --  --  --  --  --  10                                  tion  ethyl methacrylate                                                                            --  --  --  10  --  --                                        propyl acrylate --  --  --  --  --  --                                        butyl acrylate  --  --  --  20  --  20.1                                      butyl methacrylate                                                                            21  10  --  --  10  13.65                                     hexyl methacrylate                                                                            --  --  --  --  --  --                                        lauryl methacrylate                                                                           --  --  16  --  10  --                                        styrene         --  10  30  --  20  --                                        2-hydroxyethyl methacrylate                                                                     7.9                                                                               7.4                                                                               7.2                                                                               7.0                                                                               7.2                                                                             15.3                                      acetoacetoxyethyl methacrylate                                                                  0.5                                                                               2.6                                                                               1.8                                                                               2.0                                                                               0.8                                                                             --                                        t-butyl peroxy benzoate                                                                         0.6                                                                               10.0                                                                              5.0                                                                               2.0                                                                               1.0                                                                             0.7                                 Aceto-                                                                              diketene        --  --  --  --  --   0.24                               acetylating                                                                         triethylene diamine                                                                           --  --  --  --  --   0.01                               agent                                                                         Properties                                                                          nonvolatile content (%)                                                                       60  60  60  60  60  60                                        hydroxyl value  57  53  52  50  52  107                                       weight average molecular                                                                      32,300                                                                            4,200                                                                             8,320                                                                             15,000                                                                            20,800                                                                            24,500                                    weight                                                                        number of epoxy group in one                                                                  --  --  --  --  --  --                                        molecule                                                                      number of acetoacetoxy                                                                           1.25                                                                              0.85                                                                              1.15                                                                              2.31                                                                              1.28                                                                           1.2                                       group in one molecule                                                         number of cyclocarbonate                                                                      --  --  --  --  --  --                                        group in one molecule                                                   __________________________________________________________________________                          Synthesis Example                                                             52  53  54  55  56  57                                  __________________________________________________________________________    Acrylic resin No.     B.sub.2 -20                                                                       B.sub.2 -21                                                                       B.sub.2 -22                                                                       B.sub.2 -23                                                                       B.sub.2 -24                                                                       B.sub.2 -25                         Solvent                                                                             xylene          35  30  30  30  30  44.6                                      isobutyl acetate                                                                              --  --  --  --  --  5                                         ethyl acetate   --  --  --  --  --  --                                        toluene         5   10  10  10  10  --                                        Solveso #150    --  --  --  --  --  --                                  Monomer                                                                             methyl methacrylate                                                                           --  --  --  --  --  22.8                                composi-                                                                            ethyl acrylate    6.67                                                                            19  20  12  --  --                                  tion  ethyl methacrylate                                                                            --  --  --  --  24.7                                                                              --                                        propyl acrylate --  --  --  --  10.0                                                                              --                                        butyl acrylate  --  --  12  20  --  18                                        butyl methacrylate                                                                            32  10  10  --  12    3.59                                    hexyl methacrylate                                                                            --  --  --  --  5   --                                        lauryl methacrylate                                                                           --  --  --  --  --  --                                        styrene         15  --  10  20  7     5.18                                    2-hydroxyethyl methacrylate                                                                   3.5   7.5                                                                               7.7                                                                               7.2                                                                             --  --                                        acetoacetoxyethyl methacrylate                                                                --    8.5                                                                               0.2                                                                               0.3                                                                              0.8                                                                                0.43                                    t-butyl peroxy benzoate                                                                       2.2 15    0.1                                                                               0.5                                                                              0.5                                                                               0.4                                Aceto-                                                                              diketene         0.62                                                                             --  --  --  --  --                                  acetylating                                                                         triethylene diamine                                                                            0.01                                                                             --  --  --  --  --                                  agent                                                                         Properties                                                                          nonvolatile content (%)                                                                       60  60  60  60  60  50                                        hydroxyl value  18  54  55  52  0   0                                         weight average molecular                                                                      12,900                                                                            1,520                                                                             123,000                                                                           23,000                                                                            24,600                                                                            25,700                                    weight                                                                        number of epoxy group in one                                                                  --  --  --  --  --  --                                        molecule                                                                      number of acetoacetoxy                                                                        1.6   1.0                                                                               1.9                                                                                0.53                                                                            1.5                                                                               1.0                                      group in one molecule                                                         number of cyclocarbonate                                                                      --  --  --  --  --  --                                        group in one molecule                                                   __________________________________________________________________________                          Synthesis Example                                                             58  59  60  61  62  63                                  __________________________________________________________________________    Acrylic resin No.     B.sub.3 -1                                                                        B.sub.3 -2                                                                        B.sub.3 -3                                                                        B.sub.3 -4                                                                        B.sub.3 -5                                                                        B.sub.3 -6                          Solvent                                                                             xylene          51.59                                                                             50.29                                                                             50.2                                                                              48.18                                                                             45.6                                                                              45.34                                     isobutyl acetate                                                                              --  --  --  --  --  --                                        ethyl acetate   --  --  --  --  --  --                                        toluene         --  --  --  --  4   4                                         Solveso #150    --  --  --  --  --  --                                  Monomer                                                                             methyl methacrylate                                                                           12.6                                                                              20.4                                                                              20.3                                                                              20.0                                                                              22.86                                                                             --                                  composi-                                                                            ethyl methacrylate                                                                            --  --   9.9                                                                              --  --  18.18                               tion  butyl acrylate  10.4                                                                              15.3                                                                              15.3                                                                              15.2                                                                              10  --                                        butyl methacrylate                                                                            10.4                                                                              --  --  9.1  3.57                                                                             15                                        hexyl methacrylate                                                                            --  9.4 --  --  --  --                                        lauryl methacrylate                                                                           --  --  --  --  --  --                                        styrene         8.3 --  --  --  --  10                                        2-hydroxyethyl methacrylate                                                                   5.5 3.4  3.4                                                                              4.6 5.2 6.3                                       4-methacryloyloxymethyl-1,3-                                                                   0.53                                                                              0.55                                                                              0.44                                                                              0.92                                                                              0.37                                                                              0.52                                     dioxolane-2-on                                                                t-butyl peroxy benzoate                                                                        0.68                                                                              0.66                                                                              0.46                                                                             2.0 0.4  0.66                               Prop- nonvolatile content (%)                                                                       47.7                                                                              49.1                                                                              49.3                                                                              49.8                                                                              50  50                                  erties                                                                              hydroxyl value  50  30  30  40  45  55                                        weight average molecular                                                                      20,600                                                                            19,600                                                                            24,300                                                                            9,750                                                                             25,200                                                                            21,000                                    weight                                                                        number of epoxy group in one                                                                  --  --  --  --  --  --                                        molecule                                                                      number of acetoacetoxy                                                                        --  --  --  --  --  --                                        group in one molecule                                                         number of cyclocarbonate                                                                      1.2 1.2  1.2                                                                              1.0 1.0 1.2                                       group in one molecule                                                   __________________________________________________________________________                          Synthesis Example                                                             64  65  66   67  68  69                                 __________________________________________________________________________    Acrylic resin No.     B.sub.3 -7                                                                        B.sub.3 -8                                                                        B.sub.3 -9                                                                         B.sub.3 -10                                                                       B.sub.3 -11                                                                       B.sub.3 -12                        Solvent                                                                             xylene          30  20  30   30  30  30                                       isobutyl acetate                                                                              --  --  --   --  --  --                                       ethyl acetate   --  --  --   --  --  --                                       toluene         10  10  10   10  10  10                                       Solveso #150    --  10  --   --  --  --                                 Monomer                                                                             methyl methacrylate                                                                           30.07                                                                             20  --   20.12                                                                             12.2                                                                              19                                 composi-                                                                            ethyl methacrylate                                                                            --  --  --   10  --  --                                 tion  butyl acrylate  --  --  --   20  20  --                                       butyl methacrylate                                                                            21  10  --   --  --  10                                       hexyl methacrylate                                                                            --  --  --   --  --  --                                       lauryl methacrylate                                                                           --  --  16   --  --  --                                       styrene         --  10  30   --  20  --                                       2-hydroxyethyl methacrylate                                                                   7.9   7.4                                                                               7.2                                                                              7.0 7.2   7.5                                    4-methacryloyloxymethyl-1,3-                                                                   0.43                                                                               2.6                                                                               1.8                                                                               0.88                                                                             0.1   8.5                                    dioxolane-2-on                                                                t-butyl peroxy benzoate                                                                       0.6 10    5.0                                                                              2.0 0.5   15.0                             Prop- nonvolatile content (%)                                                                       60  60  60   60  60  60                                 erties                                                                              hydroxyl value  57  53  52   50  52  54                                       weight average molecular                                                                      32,000                                                                            4,400                                                                             8,400                                                                              15,200                                                                            22,300                                                                            1,530                                    weight                                                                        number of epoxy group in one                                                                  --  --  --   --  --  --                                       molecule                                                                      number of acetoacetoxy                                                                        --  --  --   --  --  --                                       group in one molecule                                                         number of cyclocarbonate                                                                       1.25                                                                               1.2                                                                                1.15                                                                            1.2 0.2   1.2                                    group in one molecule                                                   __________________________________________________________________________                                       Synthesis Example                                                             70  71  72                                 __________________________________________________________________________                 Acrylic resin No.     B.sub.3 -13                                                                       B.sub.3 -14                                                                       B.sub.3 -15                                     Solvent                                                                             xylene          30  45.32                                                                             44.98                                                 isobutyl acetate                                                                              --  --  --                                                    ethyl acetate   --  --  --                                                    toluene         10  4.0 3.9                                                   Solveso #150    --  --  --                                              Monomer                                                                             methyl methacrylate                                                                           18.95                                                                             --  25.2                                            composi-                                                                            ethyl methacrylate                                                                            --  18.2                                                                              --                                              tion  butyl acrylate  --  --  12.6                                                  butyl methacrylate                                                                            20  21.3                                                                              --                                                    hexyl methacrylate                                                                            --  --  5.1                                                   lauryl methacrylate                                                                           --  --  --                                                    styrene         20  10  5.5                                                   2-hydroxyethyl methacrylate                                                                   --  --  --                                                    4-methacryloyloxymethyl-1,3-                                                                   0.55                                                                              0.52                                                                              0.82                                                 dioxolane-2-on                                                                t-butyl peroxy benzoate                                                                       0.5  0.66                                                                             1.9                                             Prop- nonvolatile content (%)                                                                       60  50  51                                              erties                                                                              hydroxyl value  0   0   0                                                     weight average molecular                                                                      24,300                                                                            21,100                                                                            12,500                                                weight                                                                        number of epoxy group in one                                                                  --  --  --                                                    molecule                                                                      number of acetoacetoxy                                                                        --  --  --                                                    group in one molecule                                                         number of cyclocarbonate                                                                      1.2 1.2 1.1                                                   group in one molecule                                      __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________                       Example No.                                                                   1    2     3     4     5                                   __________________________________________________________________________    Structure of pigment dispersing agent                                                             A.sub.1 -B.sub.1                                          Pigment dispersing agent No.                                                                      1    2     3     4     5                                  Solvent                                                                             butanol        17.05                                                                              17.32                                                                               18.0                                                                              --    --                                        ethanol      --   --    --    --    --                                  Component                                                                           imino bispropyl amine                                                                         0.65                                                                            --    --    --    --                                  A.sub.1                                                                             triethylene tetramine                                                                      --   --    --    --    --                                        Epomine SP006.sup.1                                                                        --      0.98                                                                             --    --    --                                        Epomine SP012.sup.1                                                                        --   --    --    --    --                                        Epomine SP018.sup.1                                                                        --   --      1.9 --    --                                        Epomine SP200.sup.1                                                                        --   --    --      4.5 --                                        Epomine SP300.sup.1                                                                        --   --    --    --      2.5                                     polypropylene polyamine                                                                    --   --    --    --    --                                        PA06.sup.2                                                              Component                                                                           component B No.                                                                            B.sub.1 -1                                                                         B.sub.1 -2                                                                          B.sub.1 -3                                                                          B.sub.1 -4                                                                          B.sub.1 -5                          B     formulating amount                                                                           82.3                                                                               81.7                                                                                80.1                                                                                95.5                                                                                97.5                              Properties                                                                          A.sub.1 /B mol ratio                                                                       1/2  1/3     1/1.8                                                                               1/1.5                                                                               1/7.7                                   amine value  17   21    40    79    44                                        nonvolatile content (%)                                                                    50   50    50    60    60                                        hydroxyl value of                                                                          40   70    30    77    50                                        component B                                                                   molecular weight of                                                                        5,000                                                                              10,000                                                                              25,000                                                                              80,000                                                                              90,000                                    component B                                                                   number of reactive groups                                                                    1.2                                                                                1.0   1.1   1.7   1.7                                     in component B.sup.3                                                    Reaction                                                                            A.sub.1 -B                                                                          temper-                                                                              120  100   120   60    60                                  conditions                                                                          reaction                                                                            ature (°C.)                                                            time (Hr)                                                                             2    4     4    12    12                                  __________________________________________________________________________                        Example No.                                                                   6      7      8      9                                    __________________________________________________________________________    Structure of pigment dispersing agent                                                              A.sub.1 -B.sub.1                                                                            A.sub.1 -B.sub.2                           Pigment dispersing agent No.                                                                       6      7      8      9                                   Solvent                                                                              butanol      --     --     --     --                                          ethanol      --     --     --     --                                   Component                                                                            imino bispropyl amine                                                                      --     --     --     --                                   A.sub.1                                                                              triethylene tetramine                                                                      --     --     --     --                                          Epomine SP006.sup.1                                                                        --     --     --        0.74                                     Epomine SP012.sup.1                                                                        --     --     --     --                                          Epomine SP018.sup.1                                                                        --     --        4.13                                                                              --                                          Epomine SP200.sup.1                                                                          4.0  --     --     --                                          Epomine SP300.sup.1                                                                        --       2.0  --     --                                          polypropylene polyamine                                                                    --     --     --     --                                          PA06.sup.2                                                             Component                                                                            component B No.                                                                            B.sub.1 -6                                                                           B.sub.1 -7                                                                           B.sub.2 -1                                                                           B.sub.2 -2                           B      formulating amount                                                                           96.0   98.0   95.87                                                                                99.26                              Properties                                                                           A.sub.1 /B mol ratio                                                                         1/4.7                                                                               1/22  1/1    1/2                                         amine value  70     35     109    14                                          nonvolatile content (%)                                                                    60     60     50     50                                          hydroxyl value of                                                                          19     27     50     10                                          component B                                                                   molecular weight of                                                                        30,000 40,000 19,500 21,050                                      component B                                                                   number of reactive groups                                                                    1.0    1.0    1.2    1.2                                       in component B.sup.3                                                   Reaction                                                                             A.sub.1 -B                                                                          temper-                                                                              60     60     60     60                                   conditions                                                                           reaction                                                                            ature (°C.)                                                            time (Hr)                                                                            12     12      2      2                                   __________________________________________________________________________                       Example No.                                                                   10    11    12    13    14                                 __________________________________________________________________________    Structure of pigment dispersing agent                                                             A.sub.1 -B.sub.2                                          Pigment dispersing agent No.                                                                     10    11    12    13    14                                 Solvent                                                                             butanol      --    --    --    --    --                                       ethanol      --    --    --    --    --                                 Component                                                                           imino bispropyl amine                                                                      --    --    --    --    --                                 A.sub.1                                                                             triethylene tetramine                                                                      --    --    --    --       0.24                                  Epomine SP006.sup.1                                                                        --    --    --    --    --                                       Epomine SP012.sup.1                                                                        --    --    --    --    --                                       Epomine SP018.sup.1                                                                           1.74                                                                                1.74                                                                               1.4 --    --                                       Epomine SP200.sup.1                                                                        --    --    --       5.12                                                                             --                                       Epomine SP300.sup.1                                                                        --    --    --    --    --                                       polypropylene polyamine                                                                    --    --    --    --    --                                       PA06.sup.2                                                              Component                                                                           component B No.                                                                            B.sub.2 -3                                                                          B.sub.2 -4                                                                          B.sub.2 -5                                                                          B.sub.2 -6                                                                          B.sub.2 -7                         B     formulating amount                                                                           98.26                                                                               98.26                                                                               98.6                                                                                94.88                                                                               99.76                            Properties                                                                          A.sub.1 /B mol ratio                                                                         1/2.5                                                                               1/2.5                                                                               1/2.5                                                                               1/2.5                                                                             1/3                                      amine value  46    46    37    134    7                                       nonvolatile content (%)                                                                    50    50    50    50    50                                       hydroxyl value of                                                                          20    30    30    30    40                                       component B                                                                   molecular weight of                                                                        19,800                                                                              20,100                                                                              24,900                                                                              35,700                                                                              9,820                                    component B                                                                   number of reactive groups                                                                    1.2   1.2   1.2   1.2   1.0                                    in component B.sup.3                                                    Reaction                                                                            A.sub.1 -B                                                                          temper-                                                                              60    60    60    60    60                                 conditions                                                                          reaction                                                                            ature (°C.)                                                            time (Hr)                                                                             2     2     2     2     2                                 __________________________________________________________________________                         Example No.                                                                   15     16     17     18                                  __________________________________________________________________________    Structure of pigment dispersing agent                                                               A.sub.1 -B.sub.2                                        Pigment dispersing agent No.                                                                       15     16     17     18                                  Solvent                                                                              butanol       --     --       10.0 --                                         ethanol       --     --       6.7  --                                  Component                                                                            imino bispropyl amine                                                                       --     --     --     --                                  A.sub.1                                                                              triethylene tetramine                                                                       --     --     --     --                                         Epomine SP006.sup.1                                                                           0.5  --     --     --                                         Epomine SP012.sup.1                                                                         --     --     --     --                                         Epomine SP018.sup.1                                                                         --        1.74                                                                              --     --                                         Epomine SP200.sup.1                                                                         --     --     --        1.74                                    Epomine SP300.sup.1                                                                         --     --     --     --                                         polypropylene polyamine                                                                     --     --        1.05                                                                              --                                         PA06.sup.2                                                             Component                                                                            component B No.                                                                             B.sub.2 -8                                                                           B.sub.2 -9                                                                           B.sub.2 -10                                                                          B.sub.2 -11                         B      formulating amount                                                                            99.5   98.26                                                                                82.25                                                                                98.26                             Properties                                                                           A.sub.1 /B mol ratio                                                                        1/3    1/5    1/2     1/10                                      amine value   14     37     21     37                                         nonvolatile content (%)                                                                     50     50     50     50                                         hydroxyl value of                                                                           40     50     50     62                                         component B                                                                   molecular weight of                                                                         19,900 9,800  14,000 5,300                                      component B                                                                   number of reactive groups                                                                     1.0    1.0    1.0    0.8                                      in component B.sup.3                                                   Reaction                                                                             A.sub.1 -B                                                                           temper-                                                                              60     60     60     60                                  conditions                                                                           reaction                                                                             ature (°C.)                                                            time (Hr)                                                                             2      2      2      2                                  __________________________________________________________________________                           Example No.                                                                   19    20     21    22                                  __________________________________________________________________________    Structure of pigment dispersing agent                                                                 A.sub.1 -B.sub.2                                                                           A.sub.1 -B.sub.3                         Pigment dispersing agent No.                                                                         19    20     21    22                                  Solvent                                                                             butanol            21.37                                                                               20.73                                                                              --    --                                        ethanol          --    --     --    --                                  Component                                                                           imino bispropyl amine                                                                          --    --     --    --                                  A.sub.1                                                                             triethylene tetramine                                                                          --    --     --    --                                        Epomine SP006.sup.1                                                                            --    --     --    --                                        Epomine SP012.sup.1                                                                            --       0.77                                                                              --    --                                        Epomine SP018.sup.1                                                                               1.33                                                                             --        4.13                                                                                1.74                                   Epomine SP200.sup.1                                                                            --    --     --    --                                        Epomine SP300.sup.1                                                                            --    --     --    --                                        polypropylene polyamine PA06.sup.2                                                             --    --     --    --                                  Component                                                                           component B No.  B.sub.2 -12                                                                         B.sub.2 -13                                                                          B.sub.3 -1                                                                          B.sub.3 -2                          B     formulating amount                                                                                77.3                                                                               78.5   95.87                                                                               98.26                             Properties                                                                          A.sub.1 /B mol ratio                                                                           1/2   1/3    1/1     1/2.5                                   amine value      35    20     109   46                                        nonvolatile content (%)                                                                        40    40     50    50                                        hydroxyl value of component B                                                                  45    55     50    30                                        molecular weight of component B                                                                26,100                                                                              20,500 20,600                                                                              19,600                                    number of reactive groups                                                                        1.0   1.2    1.2   1.2                                     in component B.sup.3                                                    Reaction                                                                            A.sub.1 -B                                                                            temperature (°C.)                                                               60    60     80    80                                  conditions                                                                          reaction                                                                              time (Hr)                                                                               2     2      5     5                                  __________________________________________________________________________                           Example No.                                                                   23    24    25     26                                  __________________________________________________________________________    Structure of pigment dispersing agent                                                                 A.sub.1 -B.sub.3                                      Pigment dispersing agent No.                                                                         23    24    25     26                                  Solvent                                                                             butanol          --    --      21.37                                                                                20.73                                   ethanol          --    --    --     --                                  Component                                                                           imino bispropyl amine                                                                          --    --    --     --                                  A.sub.1                                                                             triethylene tetramine                                                                          --       0.24                                                                             --     --                                        Epomine SP006.sup.1                                                                            --    --    --     --                                        Epomine SP012.sup.1                                                                            --    --    --        0.77                                   Epomine SP018.sup.1                                                                              1.4 --       1.33                                                                              --                                        Epomine SP200.sup.1                                                                            --    --    --     --                                        Epomine SP300.sup.1                                                                            --    --    --     --                                        polypropylene polyamine PA06.sup.2                                                             --    --    --     --                                  Component                                                                           component B No.  B.sub.3 -3                                                                          B.sub.3 -4                                                                          B.sub.3 -5                                                                           B.sub.3 -6                          B     formulating amount                                                                               98.6                                                                                99.76                                                                               77.3   78.5                              Properties                                                                          A.sub.1 /B mol ratio                                                                             1/2.5                                                                             1/3   1/2    1/3                                       amine value      37     7    35     20                                        nonvolatile content (%)                                                                        50    50    40     40                                        hydroxyl value of component B                                                                  30    40    45     55                                        molecular weight of component B                                                                24,300                                                                              9,750 25,200 21,000                                    number of reactive groups                                                                        1.2   1.0   1.0     1.2                                    in component B.sup.3                                                    Reaction                                                                            A.sub.1 -B                                                                            temperature (°C.)                                                               80    80    100    90                                  conditions                                                                          reaction                                                                              time (Hr)                                                                               5     5     4      4                                  __________________________________________________________________________

    TABLE 6      Example No. 27 28 29 30 31 32 33 34 35 36 37 38 39 40       Structure of pigment dispersing agent A.sub.2 -B.sub.1 -C.sub.1     A.sub.2 -B.sub.1 -C.sub.2 A.sub.2 -B.sub.1 -C.sub.3 A.sub.2 -B.sub.1     -C.sub.4 A.sub.2 -B.sub.1 -C.sub.5 A.sub.2 -B.sub.1 -C.sub.6 A.sub.2     -B.sub.2 -C.sub.1 A.sub.2 -B.sub.2 -C.sub.2 A.sub.2 -B.sub.2 -C.sub.3     Pigment dispersing agent No. 27 28 29 30 31 32 33 34 35 36 37 38 39 40     Solvent xylene 10.7 -- 29.1 6.81 10.5 8.7 -- -- 7.7 -- -- -- -- --     butanol 7.0 18 5 -- 7 9.3 2.2 1.05 10 0.57 1.79 1.53 1.3 4.5  ethanol --     -- -- 10 -- -- -- -- -- -- -- -- -- -- Component A.sub.2 imino bispropyl     amine -- -- -- 0.59 -- -- -- -- -- -- -- -- -- --  triethylene tetramine     -- -- -- -- -- -- -- -- -- 0.82 -- -- -- --  Epomine SP006.sup. 1) 1.7     -- -- -- -- -- -- -- -- -- 2.68 -- -- --  Epomine SP012.sup. 1) -- 1.9     -- -- 1.3 -- -- 1.71 -- -- -- -- -- 1.8  Epomine SP018.sup. 1) -- -- 1.0     -- -- -- -- -- 1.6 -- -- 2.29 1.95 --  Epomine SP200.sup. 1) -- -- -- --     -- -- -- -- -- -- -- -- -- --  Epomine SP300.sup. 1) -- -- -- -- -- --     -- -- -- -- -- -- -- --  polypropylene -- -- -- -- -- 1.8 1.1 -- -- --     -- -- -- --  polyamine PA06.sup. 2) Component B component B No. B.sub.1     -2 B.sub.1 -3 B.sub.1 -6 B.sub.1 -1 B.sub.1 -3 B.sub.1 -2 B.sub.2 -1     B.sub.2 -14 B.sub.2 -19 B.sub.2 -15 B.sub.2 -16 B.sub.2 -17 B.sub.2 -18     B.sub.2 -5  formulating amount 46.3 64.6  57.5 37.5 46.4 50.5 74.3 77.0     71.0 76.71 62.0 63.61 56.32 74.6 Component C component C No. C.sub.1     C.sub.2 -2 C.sub.3 C.sub.4 C.sub.5 C.sub.6 C.sub.1 C.sub.2 -1 C.sub.2 -3 C     .sub.2 -2 C.sub.2 -3 C.sub.2 -4 C.sub.2 -5 C.sub.3  formulating amount     34.3 15.5 7.4 45.1 34.8 29.7 22.4 20.24 9.7 21.9 33.53 32.57 40.43 19.1     Properties A.sub.2 /B mol ratio 1/1 1/1 1/2 1/1 1/1 1/1 1/1 1/1 1/2     1/3.3 1/1.7 1/3.3 1/2.6 1/1  A.sub.2 /C mol ratio 1/2 1/5 1/3 1/1 1/4     1/2 1/2 1/1 1/3 1/2.7 1/1.5 1/5   1/3.4 1/3  amine value 36 40 26 15 27     46 28 30 34 21 47 40 34 38  nonvolatile content (%) 50 50 40 50 50 50 50     60 50 60 60 60 60 50  hydroxyl value of component 70 30 19 40 30 70 50     57 107 53 52 50 52 30  B  molecular weight of 10,000 25,000 30,000 5,000 2     5,000 10,000 19,500 32,300 24,500 4,200 8,320 15,000 20,800 24,900     component B  number of reactive groups in 1.0 1.1 1.0 1.2 1.1 1.0 1.2     1.25 1.2 0.85 1.15 2.31 1.28 1.2  component B.sup. 3)  molecular weight     of  3,700  1,200  2,580 6,000  4,670  2,960  3,700  8,500  2,250 1,200     2,250  5,120 11,200  2,580  component C Reaction A.sub.2 -B temperature     (°C.) 120 120 100 120 120 120 60 60 60 60 60 60 60 60 conditions     reaction time (Hr) 4 4 4 4 4 4 2 2 2 2 2 2 2 2 Reaction A.sub.2 -C     temperature (°C.) 50 50 30 60 30 60 30 60 60 50 60 60 60 30     conditions reaction time (Hr) 2 2 4 2 2 2 4 2 3 2 2 2 2 3       Example No. 41 42 43 44 45 46 47 48 49 50 51 52 53       Structure of pigment dispersing agent A.sub.2 -B.sub.2 -C.sub.4     A.sub.2 -B.sub.2 -C.sub.5 A.sub.2 -B.sub.2 -C.sub.6 A.sub.2 -B.sub.3     -C.sub.1 A.sub.2 -B.sub.3 -C.sub.2 A.sub.2 -B.sub.3 -C.sub.2 A.sub.2     -B.sub.3 -C.sub.3 A.sub.2 -B.sub.3 -C.sub.4 A.sub.2 -B.sub.3 -C.sub.5     A.sub.2 -B.sub.3 -C.sub.6 Pigment dispersing agent No. 41 42 43 44 45 46 4     7 48 49 50  51 52 53 Solvent xylene -- 12.8 7.1 13.7 -- -- -- -- 9.4     12.7 -- 23.8 8  butanol 4.5 5 -- 6 1.05 0.57 1.79 1.53 12 5 3.8 5 10     ethanol -- -- 10.0 -- -- -- -- -- -- -- -- -- -- Component A.sub.2 imino     bispropyl amine -- -- 0.6 -- -- -- -- -- -- -- -- -- --  triethylene     tetramine -- -- -- -- -- 0.82 -- -- -- -- -- -- --  Epomine SP006.sup.     1) -- -- -- -- -- -- 2.68 -- -- -- -- -- --  Epomine SP012.sup. 1) -- --     -- 1.0 1.71 -- -- -- -- 1.6 -- -- --  Epomine SP018.sup. 1) 1.4 -- -- --     -- -- -- 2.29 1.3 -- 1.8 -- --  Epomine SP200.sup. 1) -- -- -- -- -- --     -- -- -- -- -- 6.8 --  Epomine SP300.sup. 1) -- -- -- -- -- -- -- -- --     -- -- -- --  polypropylene -- 1.7 -- -- -- -- -- -- -- -- -- -- 2.0     polyamine PA06.sup.2) Component B component B No. B.sub.2 -12 B.sub.2     -20 B.sub.2 -16 B.sub.3 -1 B.sub.3 -7 B.sub.3 -8 B.sub.3 -9 B.sub.3 -10     B.sub. 3 -3 B.sub.3 -10 B.sub.3 -6 B.sub.3 -4 B.sub.3 -9  formulating     amount 79.1 59.2 60.8 69.4 77.0 76.71 62.0 63.61 71.8 64.2 84.4 53.7     46.7 Component C component C No. C.sub.4 C.sub.5 C.sub.6 C.sub.1 C.sub.2     -1 C.sub.2 -2 C.sub.2 -3 C.sub.2 -4 C.sub.2 -3 C.sub.3 C.sub.4 C.sub.5     C.sub.6  formulating amount 15.0 21.3 21.5 9.9 20.24 21.9 33.53 32.57     5.5 16.5 10.0 10.7 33.3 Properties A.sub.2 /B mol ratio 1/2 1/1 1/1 1/2     1/1 1/3.3 1/1.7 1/3.3 1/2 1/2 1/2 1/4 1/1  A.sub.2 /C mol ratio 1/2 1/1     1/1 1/2 1/1 1/2.7 1/1.5 1/5   1/2 1/3 1/1 1/2 1/2  amine value 29 36 15     26 30 21 47 40 34  34 38 179 61  nonvolatile content (%) 50 50 50 40 60     60 60 60 40 50 50 40 50  hydroxyl value of component 45 18 52 50 57 53     52 50 30 50 55 40 52  B  molecular weight of 26,100 12,900 8,320 20,600     32,000 4,400 8,400 15,200 24,300 15,200 21,000 9,750 8,400  component B     number of reactive groups in 1.0 1.6 1.15 1.2 1.25 1.2 1.15 1.2 1.2 1.2     1.2 1.0 1.15  component B.sup. 3)  molecular weight of  6,000  4,670     2,960  3,700  8,500 1,200 2,250  5,120  2,250  2,580  6,000 4,670 2,960     component C Reaction A.sub.2 -B temperature (°C.) 80 70 60 70 80     80 80 80 80 100 90 80 70 conditions reaction time (Hr) 1 2 2 2 5 5 5 5 5     3 4 5 4 Reaction A.sub.2 -C temperature (°C.) 50 30 60 30 50 50     60 60 50 30 50 30 60 conditions reaction time (Hr) 3 4 2 4 2 2 2 2 3 3 4     3 3       Note: .sup.1) Epomine: trade name of polyethylene imine having the     following molecular weight and amine value, made by Nippon Shokubai     Kagaku Kogyo K. K. Trade namer Molecular weight Amine value  Epomine     SP006   600 1050 Epomine SP012  1,200 1050 Epomine SP018  1,800 1050     Epomine SP200 10,000 1050 Epomine SP300 30,000 1050 .sup.2) trade name,     made by Toso K.K., molecular weight: 600, amine value: 1100 .sup.3)     Number of reaction group in component B is number of glycidyl, acetoaceto     xy or cyclocarbonate groups per one molecule of component B

    TABLE 7       Application Example   1  2  3  4  5  6  7  8  9  10  11  12  13  14     15      16     Pigment dispersing agent No..sup.1)  1  2  3  4  5  6  7  8  9  10  11     12  13  14  15  16 Acrylic resin No..sup.2) AC-1 AC-2 AC-3 AC-4 AC-5     AC-6 AC-7 AC-8 AC-8 AC-8 AC-8 AC-8 AC-8 AC-8 AC-8 AC-8 Polyester resin     No..sup.3) -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Formulation     pigment dispersing agent 16.0  6.0 15.0  2.9  1.2  2.9  2.9  1.9  7.5     3.8  3.8  3.8  1.9  3.8 11.3  7.5 of disper- acrylic resin 40.0 36.7     29.2 52.0 20.8 52.0 52.0 60.8 55.2 58.9 58.9 58.9 60.8 21.3 51.4 55.2     sion paste polyester resin -- -- -- -- -- -- -- -- -- -- -- -- -- -- --     --  xylene 18.0 22.3 20.8 13.3 30.0 22.3 22.3  9.2  9.2  9.2  9.2  9.2     9.2 18.6  9.2  9.2  ethyl cellosolve -- -- -- -- -- -- --  9.3  9.3  9.3      9.3  9.3  9.3 18.7  9.3  9.3  butyl cellosolve -- -- -- -- 10.4  4.0     4.0 -- -- -- -- -- -- -- -- --  cellosolve acetate 18.0 20.0 20.0 13.0     -- -- -- -- -- -- -- -- -- -- -- --  titanium dioxide JR 602.sup.4) --     -- -- -- 37.6 --  -- -- -- -- -- -- -- 37.6 -- --  carbon black FW-200.su     p.5)  8.0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- --  Fosterperm     Yellow-H3G.sup.6) -- -- -- 18.8 -- -- 18.8 -- -- -- -- -- -- -- -- --     Fastogen Blue-RGA.sup.7) -- -- -- -- -- 18.8 -- -- 18.8 -- -- 18.8 -- --     -- 18.8  Paliogen Maroon L3820.sup.8) -- -- 15.0 -- -- -- -- 18.8 -- --     18.8 -- -- -- 18.8 --  Rubicron Red 500RG.sup.9) -- -- -- -- -- -- -- --     -- 18.8 -- -- 18.8 -- -- --  Paliotol Red L3670.sup.10) -- -- -- -- --     -- -- -- -- -- -- -- -- -- -- --  Paliogen Violet L-5080.sup.11) -- --     -- -- -- -- -- -- -- -- -- -- -- -- -- --  Noboperm Red F3RK-70.sup.12)     -- 15.0 -- -- -- -- -- -- -- -- -- -- -- -- -- --  Irgazine Red BPT.sup.1     3) -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Prop- amount of     pigment 100  20  50  10  2  10  10  5  20  10  10  10  5  5  30  20     erties dispersing agent of paste added (%).sup.14)  viscosity of 520 160     240  82  38  66  92 5300  3800 2400 1200 4200 1300 6000 900 4900     dispersion  paste (CP).sup.15)  storage stability good good good good     good good good good good good good good good good good good  of dispersio     n  paste.sup.16) Formula- dispersion paste 30.5 52.0 52.0 44.2 59.1 44.2     44.2 44.2 44.2 44.2 59.9 44.2 44.2 59.1 44.2 44.2 tion of acrylic resin     40.6 23.8 23.8 24.2 20.1 24.2 24.2 29.0 29.0 29.0 16.0 29.0 29.0 24.1     29.0 29.0 paint polyester resin -- -- -- -- -- -- -- -- -- -- -- -- --     -- -- --  melamine resin.sup.17) 24.4 19.5 19.5 20.8 13.9 20.8 20.8 20.8     20.8 20.8 20.1 20.8 20.8 13.9 20.8 20.8  leveling agent.sup.18)  0.6     0.6  0.6  0.6  0.5  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6     0.6  thinner.sup.19)  3.9  4.1  4.1 10.2  6.4 10.2 10.2  5.4  5.4  5.4     3.4  5.4  5.4  2.3  5.4  5.4 Prop- 30°  specular gloss  90  80     87  84  88  84  82  83  85  86  82  87  88  82  85  80 erties humidity     good good good good good good good good good good good good good good     good good of paint resistance.sup.20) film weather  82  85  89  88  90     91  85  81  86  89  88  85  86  88  85  89  resistance.sup.21)  absence     or ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab-     presence of sence sence sence sence sence sence sence sence sence sence     sence sence sence sence sence sence  bleeding.sup.22)       Application Example   17  18  19  20  21  22  23  24  25  26  27  28     29  30  31      32                                                             Pigment     dispersing agent No..sup.1)  17   18  19  20  21  22  23  24  25  26  27      27  28  29  29  30 Acrylic resin No..sup.2) AC-2 AC-8 AC-3 AC-9 AC-8     AC-8 AC-8 AC-8 AC-8 AC-8 AC-1 -- AC-6 AC-2 -- AC-6 Polyester resin     No..sup.3) -- -- -- -- -- -- -- -- -- -- -- PE-1 -- -- PE-2 -- Formulatio     n pigment dispersing agent  6.0 13.4  6.0  6.0  1.9  3.8  3.8  3.8  7.5  7     .5 16.0  20  6.0 18.8 23.5 16.0 of disper- acrylic resin 36.7 67 36.7     36.7 60.8 58.9 58.9 21.3 36.7 36.7 40.0 -- 36.7 29.2 -- 40.0 sion paste     polyester resin -- -- -- -- -- -- -- -- -- -- --  50 -- -- 36.5 --     xylene 22.3  6.4 22.3 22.3  9.2  9.2  9.2 18.6 20.0 20.0 18.0  10 22.3     17.0 -- 18.0  ethyl cellosolve --  6.4 -- --  9.3  9.3  9.3 18.7 -- --     -- -- -- -- -- --  butyl cellosolve -- -- -- -- -- -- -- -- -- -- -- --     -- -- -- --  cellosolve acetate 20.0 -- 20.0 20.0 -- -- -- -- 20.8 20.8     18.0  10 20.0 20.0 -- 18.0  titanium dioxide JR 602.sup.4) -- -- -- --     -- -- -- 37.6 -- -- -- -- -- -- -- --  carbon black FW-200.sup.5) --     6.7 -- -- -- -- -- -- -- --  8.0  10 -- -- --      8.0  Fosterperm Yellow-H3G.sup.6) -- -- -- -- -- -- -- -- -- -- -- --     -- -- -- --  Fastogen Blue-RGA.sup.7) -- -- -- -- -- -- 18.8 -- -- -- --     -- -- -- -- --  Paliogen Maroon L3820.sup.8) -- -- -- -- 18.8 18.8 -- --     -- -- -- -- -- 15.0 18.8 --  Rubicron Red 500RG.sup.9) -- -- -- 15.0 --     -- -- -- 15.0 -- -- -- -- -- -- --  Paliotol Red L3670.sup.10) -- -- --     -- -- -- -- -- -- -- -- -- -- -- -- --  Paliogen Violet L-5080.sup.11)     -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --  Noboperm Red F3RK-70.sup     .12) 15.0 -- -- -- -- -- -- -- -- 15.0 -- -- -- -- -- --  Irgazine Red     BPT.sup.13) -- -- 15.0 -- -- -- -- -- -- -- -- -- 15.0 -- -- -- Prop-     amount of pigment  20 100  20  20  5  10  10  5  20  20 100 100  20  50     50 100 erties dispersing agent of paste added (%).sup.14)  viscosity of     270 2500  240 350 5600  1800  3800  6300  2100  1500  420 460 260 320     410 480  dispersion  paste (CP).sup.15)  storage stability good good     good good good good good good good good good good good good good good     of dispersion  paste.sup.16) Formula- dispersion paste 52.0 59.9 52.0     52.0 44.2 59.9 44.2 59.1 52.0 52.0 30.5 25.9 52.0 52.0 46.7 30.5 tion of     acrylic resin 23.8 16.0 23.8 23.8 29.0 16.0 29.0 24.1 23.8 23.8 40.6 --     23.8 23.8 -- 40.6 paint polyester resin -- -- -- -- -- -- -- -- -- -- --     43.1 -- -- 26.8 --  melamine resin.sup.17) 19.5 20.1 19.5 19.5 20.8 20.1     20.8 13.9 19.5 19.5 24.4 25.9 19.5 19.5 21.9 24.4  leveling agent.sup.18)       0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6     0.6  0.6  thinner.sup.19)  4.1  3.4  4.1  4.1  5.6  3.2  4.9  2.0  4.1     4.1  3.9  4.5  4.1  4.1  4.0  3.9 Prop- 30° specular gloss  85     80  87  87  83  79  85  81  84  86  84  88  85  87  90  88 erties     humidity good good good good good good good good good good good good     good good good good of paint resistance.sup.20) film weather  88  88  90      87  80  89  84  85  88  87  90  92  90  84  88  84  resistance.sup.21)     absence or ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab- ab-     ab-  presence of sence sence sence sence sence sence sence sence sence     sence sence sence sence sence sence sence  bleeding.sup.22)       Application Example   33  34  35  36  37  38  39  40  41  42  43  44     45  46  47      48                                                             Pigment     dispersing agent No..sup.1)  31  32  33  33  33  34  34  35  36  37  38     39  40  40  40  41 Acrylic resin No..sup.2) AC-6 AC-6 AC-8 -- -- -- AC-9     AC-9 -- AC-9 AC-9 AC-9 AC-9 -- -- AC-9 Polyester resin No..sup.3) -- --     -- PE-1 PE-2 PE-1 --  -- PE-1 -- -- -- -- PE-1 PE-2 -- Formulation     pigment dispersing agent  9.0  6.0  6.0  7.5  7.5  5.8  7.5  6.0  5.8     5.8  5.8  5.8  6.0  7.5  7.5 21.0 of disper- acrylic resin 34.2 36.7     36.7 -- -- -- 34.2 36.7 -- 49.1 49.1 49.1 36.7 -- -- 24.2 sion paste     polyester resin -- -- -- 45.8 45.8 49.1 -- -- 49.1 -- -- -- -- 45.8 45.8     --  xylene 21.8 22.3 22.3 12.9 12.9 22.3 23.3 22.3 22.3 22.3 22.3 22.3     22.3 12.9 12.9 19.8  ethyl cellosolve -- -- -- -- -- -- -- -- -- -- --     -- -- -- -- --  butyl cellosolve -- -- -- -- -- -- -- -- -- --  -- -- --     -- -- --  cellosolve acetate 20.0 20.0 20.0  15  15  4.0 20.0 20.0  4.0     4.0  4.0  4.0 20.0  15  15 20.0  titanium dioxide JR 602.sup.4) -- -- --     -- -- -- -- -- -- -- -- -- -- -- -- --  carbon black FW-200.sup.5) -- --     -- -- -- -- -- -- -- -- -- -- -- -- -- --  Fosterperm Yellow-H3G.sup.6)     -- -- -- -- -- -- 15.0 -- -- -- -- -- -- -- -- --  Fastogen Blue-RGA.sup.     7) 15.0 -- -- -- -- -- -- -- -- -- -- 18.8 -- -- -- --  Paliogen Maroon     L3820.sup.8) -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 15.0  Rubicron     Red 500RG.sup.9) -- -- 15.0 18.8 18.8 -- -- -- 18.8 -- -- -- -- -- -- --      Paliotol Red L3670.sup.10) -- 15.0 -- -- -- 18.8 -- 15.0 -- -- -- -- --     -- -- --  Paliogen Violet L-5080.sup.11) -- -- -- -- -- -- -- -- -- 18.8     -- -- -- -- -- --  Noboperm Red F3RK-70.sup.12) -- -- -- -- -- -- -- --     -- -- 18.8 -- -- -- -- --  Irgazine Red BPT.sup.13) -- -- -- -- -- -- --     -- -- -- -- -- 15.0 18.8 18.8 -- Prop- amount of pigment  30  20  20  20      20  20  30  20  20  20  20  20  20  20  20  70 erties dispersing agent     of paste added (%).sup.14)  viscosity of 370 720 340 460 390 213 420 370     253 263 218 289 490 360 350 420  dispersion  paste (CP).sup.15)  storage     stability good good good good good good good good good good good good     good good good good  of dispersion  paste.sup.16) Formula- dispersion     paste 51.7 52.0 52.0 46.7 46.7 44.2 51.7 52.0 44.2 44.2 44.2 44.2 52.0     46.7 46.7 51.7 tion of acrylic resin 23.7 23.7 23.8 -- -- -- 23.7 23.8     -- 24.2 24.2 24.2 23.8 -- -- 23.7 paint polyester resin -- -- -- 26.8     26.8 24.2 -- -- 24.2 -- -- -- -- 26.8 26.8 --  melamine resin.sup.17)     19.4 19.5 19.5 21.9 21.9 20.8 19.4 19.5 20.8 20.8 20.8 20.8 19.5 21.9     21.9 19.4  leveling agent.sup.18)  0.6  0.6  0.6  0.6  0.6  0.6  0.6     0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  thinner.sup.19)  4.6  4.2     4.1  4.0  4.0 10.2  4.6  4.1 10.2 10.2 10.2 10.2  4.1  4.0  4.0  4.6     Prop- 30° specular gloss  83  86  84  86  84  82  84  82  84  83     81  80  82  83  81  84 erties humidity good good good good good good     good good good good good good good good good good of paint resistance.sup     .20) film weather  87  87  83  86  88  83  87  80  85  82  83  83  87     82  84  84  resistance.sup.21)  absence or ab- ab- ab- ab- ab- ab- ab-     ab- ab- ab- ab- ab- ab- ab- ab- ab-  presence of sence sence sence sence     sence sence sence sence sence sence sence sence sence sence sence sence     bleeding.sup.22)       Application Example   49  50   51  52  53  54  55  56  57  58  59  60  6     1  62  63      64                                                              Pigment     dispersing agent No..sup.1)  42  43  44  45  46  47  48  48  49  49  49     50  51  52  53  53 Acrylic resin No..sup.2) -- AC-9 -- -- -- AC-9 AC-9     -- AC-9 -- -- AC-9 AC-9 -- AC-9 -- Polyester resin No..sup.3) PE-1 --     PE-1 PE-1 PE-1 -- -- PE-1 -- PE-1 PE-2 -- -- PE-2 -- PE-1 Formulation     pigment dispersing agent  7.5 16.0 18.8  5.8  5.8  5.8  5.8  6.3  5.8     9.4  9.4 12.0  6.0  9.4  9.0 20 of disper- acrylic resin -- 40.0 -- --     -- 49.1 49.1 -- 49.1 -- -- 31.7 36.7 -- 34.2 -- sion paste polyester     resin 45.8 -- 39.6 49.1 49.1 -- -- 45.8 -- 45.8 45.8 -- -- 45.8 --  50     xylene 12.9 18.0 12.8 22.3 22.3 22.3 22.3 19.1 22.3  16  16 21.3 22.3     16 21.8  10  ethyl cellosolve -- -- -- -- -- -- -- -- -- -- -- -- -- --     -- --  butyl cellosolve -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --     cellosolve acetate 15.0 18.0  10  4.0  4.0  4.0  4.0  10  4.0  10  10     20.0 20.0  10 20.0  10  titanium dioxide JR 602.sup.4) -- -- -- -- -- --     -- -- -- -- -- -- -- -- -- --  carbon black FW-200.sup.5) --  8.0 -- --     -- -- -- -- -- -- -- -- -- -- --  10  Fosterperm Yellow-H3G.sup.6) -- --     -- -- -- -- -- -- -- -- -- -- -- -- -- --  Fastogen Blue-RGA.sup.7) --     -- -- -- -- -- -- -- 18.8 18.8 18.8 -- -- -- -- --  Paliogen Maroon     L3820.sup.8) -- -- 18.8 -- -- -- -- -- -- -- -- 15.0 -- -- -- --     Rubicron Red 500RG.sup.9) -- -- -- -- 18.8 -- -- -- -- -- -- -- 15.0 --     -- --  Paliotol Red L3670.sup.10) -- -- -- 18.8 -- -- -- -- -- -- -- --     -- 18.8 -- --  Paliogen Violet L-5080.sup.11) -- -- -- -- -- 18.8 -- --     -- -- -- -- -- --  15 --  Noboperm Red F3RK-70.sup.12) 18.8 -- -- -- --     -- 18.8 18.8 -- -- -- -- -- -- -- --  Irgazine Red BPT.sup.13) -- -- --     -- -- -- -- -- -- -- -- -- -- -- -- -- Prop- amount of pigment  20 100     40  20  20  20  20  20  20  20  20  40  20  20  30 100 erties dispersing     agent of paste added (%).sup.14)  viscosity of 240 440 320 218 272 282     232 420 300 700 810 490 260 510 340 490  dispersion  paste (CP).sup.15)     storage stability good good good good good good good good good good good     good good good good good  of dispersion  paste.sup.16) Formula- dispersio     n paste 46.7 30.5 46.7 44.2 44.2 44.2 44.2 46.7 44.2 46.7 46.7 51.7 52.0     46.7 51.7 25.9 tion of acrylic resin -- 40.6 -- -- -- 24.2 24.2 -- 24.2     -- -- 23.7 23.8 -- 23.7 -- paint polyester resin 26.8 -- 26.8 24.2 24.2     -- -- 26.8 -- 26.8 26.8 -- -- 26.8 -- 43.1  melamine resin.sup.17) 21.9     24.4 21.9 20.8 20.8 20.8 20.8 21.9 20.8 21.9 21.9 19.4 19.5 21.9 19.4     25.9  leveling agent.sup.18)  0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6     0.6  0.6  0.6  0.6  0.6  0.6  0.6  0.6  thinner.sup.19)  4.0  3.9  4.0     10.2 10.2 10.2 10.2  4.0 10.2  4.0  4.0  4.6  4.1  4.0  4.6  4.5 Prop-     30° specular gloss  82  82  90  80  81  80  79  82  78  81  82     81  81  82  80  80 erties humidity good good good good good good good     good good good good good good good good good of paint resistance.sup.20)     film weather  84  88  89  82  83  83  84  80  83  84  84  86  86  84  84      83  resistance.sup.21)  absence or ab- ab- ab- ab- ab- ab- ab- ab- ab-     ab- ab- ab- ab- ab- ab- ab-  presence of sence sence sence sence sence     sence sence sence sence sence sence sence sence sence sence sence     bleeding.sup.22)     Note:     .sup.1) pigment dispersing agent of Examples (Tables 5 and 6)     .sup.2) acrylic resin for film formation in Table 2     .sup.3) polyester resin for film formation in Table 1     .sup.4) titanium dioxide JR602 (made by Teikoku Kako K.K., trade name)     .sup.5) carbon black FR200 (made by Degussa AG, trade name)     .sup.6) Fosterparm Yellow H3G (benzimidazolone series organic pigment,     made by Hoechst, trade name)     .sup.7) Fastogen Blue RGA (copperphthalocyanine series organic pigment,     made by Dainippon Ink & Chemicals, Inc., trade name)     .sup.8) Paliogen Maroon L3820 (perylene series organic pigment, made by     BASF Ag, trade name)     .sup.9) Rubicron Red 500RG (quinacridone series organic pigment, made by     Toso K.K., trade name)     .sup.10) Paliotol Red L3670 (perylene series organic pigment, made by BAS     AG, trade name)     .sup.11) Paliogen Violet L5080 (thioindigo series organic pigment, made b     BASF AG, trade name)     .sup.12) Noboperm Red F3RK70 (azo series organic pigment, made by Hoechst     trade name)     .sup.13) Irgazine Red BPT (perylene series organic pigment, made by Ciba     Geigy, trade name)     .sup.14) amount of pigment dispersing agent added as solid content on     pigment (%)     .sup.15) paste viscosity: measured by means of Btype viscometer at     20° C. (unit: CP)     .sup.16) After the dispersion paste was left to stand at 50° C. fo     5 days, the viscosity was measured at 20° C. by means of Btype     viscometer (trade name, made by Tokyo Keiki K.K.). When the ratio of     initial viscosity to viscosity after 5 days is within a range of 0.9-1.4,     the storage stability is good, while when it exceeds 2.0, the property is     poor.     .sup.17) melamine resin: Uban 220 (made by Mitsui Toatsu Chemicals, Inc.,     trade name, nonvolatile content: 60%)     .sup.18) leveling agent: Modaflow (made by Monsanto Co., trade name, 10%     xylene solution)     .sup.19) thinner for dilution: cellosolve acetate/xylene = 50/50%     .sup.20) Humidity test After the test sheet was held at 50 ± 1°     C. in a moisture atmosphere of not less than 95% RH for 120 hours, it was     taken out from the above atmosphere and left to stand for 24 hours. The     good or bad humidity resistance was evaluated by the size and density of     resulting blister.     .sup.21) The 60° specular gloss was measured by means of a sunshin     carbon weathermeter after the sheet was exposed for 1000 hours according     to a method for weather acceleration test of JIS D02057.6. The property     was represented by the gloss retention (%).     .sup.22) Test for judgment of bleeding After the cured film was rubbed     with a methanol impregnated cloth several times, the film gloss or glossy     feeling was judged by the presence or absence of bleeding.     no change: no bleeding     enhancement of gloss: presence of bleeding

                                      TABLE 8                                     __________________________________________________________________________                   Comparative Example No.                                                       1   2   3   4   5    6    7                                    __________________________________________________________________________    Pigment dispersing agent No.                                                                 54  55  56  57  58   59   60                                   Solvent                                                                       xylene         --  --  --  10  --   --   --                                   butanol          18.0                                                                              2.2                                                                               18.0                                                                              19.9                                                                              2.5                                                                                 0.54                                                                              20.75                              methanol       --  --  --  --  --   --   --                                   Component A                                                                   imino bispropyl amine                                                                        --  --  --  --  --   --   --                                   triethylene tetramine                                                                        --  --  --  --  --   --   --                                   Epomine SP006  --  --  --  --  --   --   --                                   Epomine SP012  --  --  --  --  --   --      0.77                              Epomine SP018    1.9                                                                               3.4                                                                               1.9                                                                               19.9                                                                               3.77                                                                               0.36                                                                            --                                   Epomine SP200  --  --  --  --  --   --   --                                   Epomine SP300  --  --  --  --  --   --   --                                   polypropylene polyamine PA06                                                                 --  --  --  --  --   --   --                                   Component B                                                                   component B No.                                                                              B.sub.1 -8                                                                        B.sub.3 -11                                                                       B.sub.1 -9                                                                        B.sub.2 -21                                                                       B.sub.3 -12                                                                        B.sub.1 -10                                                                        B.sub.3 -14                          formulating amount                                                                             80.1                                                                              75.5                                                                              80.1                                                                              50.2                                                                              85.36                                                                              99.1                                                                               78.48                              Component C                                                                   component C No.                                                                              --  C.sub.2 -4                                                                        --  --  C.sub.2 -6                                                                         --   --                                   formulating amount                                                                           --    18.9                                                                            --  --     8.37                                                                            --   --                                   Properties                                                                    A/B mol ratio  1/1.8                                                                             1/1.7                                                                             1/1.8                                                                             1/1.8                                                                             1/16 1/1.8                                                                              1/3                                  A/C mol ratio  --  1/2.0                                                                             --  --  1/3  --   --                                   amine value    40  59  40  420 66    9   20                                   nonvolatile content (%)                                                                      50  60  50  50  60   40   40                                   hydroxyl value of                                                                            30  52  37  54  54   30    0                                   component B                                                                   molecular weight of                                                                          25,200                                                                            22,300                                                                            25,000                                                                            1,520                                                                             1,530                                                                              110,000                                                                            21,100                               component B                                                                   number of reactive groups                                                                      0.5                                                                               0.2                                                                               4.4                                                                               1.0                                                                               1.2                                                                                1.1                                                                                1.2                                in component B                                                                molecular weight of                                                                          --   5,120                                                                            --  --  800  --   --                                   component C                                                                   Reaction conditions                                                           A-B            reaction                                                       temperature (°C.)                                                                     120 80  120 120 60   120  80                                   time (Hr)       4   5   3   4   2    4    5                                   A-C            reaction                                                       temperature (°C.)                                                                     --  30  --  --  60   --   --                                   time (Hr)      --   2  --  --   2   --   --                                   Fluid property good                                                                              good                                                                              gel good                                                                              good good good                                 __________________________________________________________________________                       Comparative Example No.                                                       8    9   10  11   12   13                                  __________________________________________________________________________    Pigment dispersing agent No.                                                                     61   62  63  64   65   66                                  Solvent                                                                       xylene             --   --  --  --   --   --                                  butanol              19.8                                                                               1.1                                                                               4.5                                                                                1.84                                                                              2.5                                                                                3.6                               methanol           --   --  --  --   --   --                                  Component A                                                                   imino bispropyl amine                                                                            --   --  --  --   --   --                                  triethylene tetramine                                                                            --   --  --  --   --   --                                  Epomine SP006         0.94                                                                            --  --  --      3.75                                                                            --                                  Epomine SP012      --     1.2                                                                             --  --   --     5.5                               Epomine SP018      --   --    1.4                                                                                2.86                                                                            --   --                                  Epomine SP200      --   --  --  --   --   --                                  Epomine SP300      --   --  --  --   --   --                                  polypropylene polyamine PA06                                                                     --   --  --  --   --   --                                  Component B                                                                   component B No.    B.sub.3 -15                                                                        B.sub.2 -25                                                                       B.sub.2 -25                                                                       B.sub.3 -13                                                                        --   --                                  formulating amount   79.26                                                                              97.7                                                                              79.1                                                                              79.4                                                                             --   --                                  Component C                                                                   component C No.    --   --  C.sub.4                                                                           C.sub.2 -4                                                                         C.sub. 2 -4                                                                        C.sub.6                             formulating amount --   --    15.0                                                                              15.9                                                                               93.75                                                                              90.9                              Properties                                                                    A/B mol ratio      1/2  1/2 1/2 1/2  --   --                                  A/C mol ratio      --   --  1/2 1/2  1/1.8                                                                              1/4                                 amine value        24   25  29  49   66   96                                  nonvolatile content (%)                                                                          40   50  50  60   60   60                                  hydroxyl value of   0    0   0   0    0    0                                  component B                                                                   molecular weight of                                                                              12,500                                                                             25,700                                                                            25,700                                                                            24,300                                                                             --   --                                  component B                                                                   number of reactive groups                                                                          1.1                                                                                1.0                                                                               1.0                                                                               1.2                                                                              --   --                                  in component B                                                                molecular weight of                                                                              --   --   6,000                                                                             5,120                                                                             5,120                                                                              2,960                               component C                                                                   Reaction conditions                                                           A-B                reaction                                                   temperature (°C.)                                                                         80   60  60  80   --   --                                  time (Hr)           5    2   2   5   --   --                                  A-C                reaction                                                   temperature (°C.)                                                                         --   --  30  60   60   60                                  time (Hr)          --   --   2   2    2    2                                  Fluid property     good good                                                                              good                                                                              good good good                                __________________________________________________________________________

                                      TABLE 9                                     __________________________________________________________________________                   Comparative Application Example                                               1    2    3    4    5    6     7     8                         __________________________________________________________________________    Pigment dispersing agent No.                                                                 54   55   57   58   59   60    61    --                        Acrylic resin No.                                                                            AC-3 AC-8 AC-3 --   AC-3 AC-8  AC-8  AC-8                      Polyester resin No.                                                                          --   --   --   PE-1 --   --    --    --                        Formulation of dispersion paste                                               pigment dispersing agent                                                                     15    5.8 15    5.8 18.8 22.5  22.5  --                        acrylic resin  29.2 49.1 29.2 --   29.2 24.7  24.7  62.7                      polyester resin                                                                              --   --   --   49.1 --   --    --    --                        xylene         20.8 22.3 20.8 22.3 17.0 20.0  20.0   9.2                      ethyl cellosolve                                                                             --   --   --   --   --   --    --     9.3                      cellosolve acetate                                                                           20.0  4.0 20.0  4.0 20.0 17.8  17.8  --                        titanium dioxide JR 602                                                                      --   --   --   --   --   --    --    --                        carbon black FW-200                                                                          --   --   --   --   --   --    --    --                        Fosterperm Yellow-H3G                                                                        --   --   --   --   --   --    --    --                        Fastogen Blue-RGA                                                                            --   --   --   --   --   --    --    --                        Paliogen Maroon L3820                                                                        15.0 --   15.0 --   15.0 --    --    --                        Rubicron Red 500RG                                                                           --   --   --   --   --   --    --    --                        Paliotol Red L3670                                                                           --   --   --   18.8 --   --    --    18.8                      Noboperm Red F3RK-70                                                                         --   18.8 --   --   --   15.0  15.0  --                        Paliogen Violet L-5080                                                                       --   --   --   --   --   --    --    --                        Properties of paste                                                           amount of pigment                                                                            50   20   50   20   50   60    60    0                         dispersing agent added                                                        viscosity of dispersion                                                                      12,400                                                                             8,750                                                                              9,700                                                                              10,300                                                                             14,300                                                                             2,200 4,600 gel                       paste (CP)                                                                    storage stability of                                                                         poor poor poor poor poor good  good  poor                      dispersion paste                                                              Formulation of paint                                                          dispersion paste                                                                             52.0 44.2 52.0 44.2 52.0 52.0  52.0  44.2                      acrylic resin  23.8 24.2 23.8 --   23.8 23.8  23.8  29.0                      polyester resin                                                                              --   --   --   24.2 --   --    --    --                        melamine resin 19.5 20.8 19.5 20.8 19.5 19.5  19.5  20.8                      leveling agent  0.6  0.6  0.6  0.6  0.6  0.6   0.6   0.6                      thinner         4.1 10.2  4.1 10.2  4.1  4.1   4.1   5.4                      Properties of paint film                                                      30° specular gloss                                                                    32   64   30   51   21   82    80    56                        humidity resistance                                                                          good good good good good occurrence                                                                          occurrence                                                                          good                                                              of blister                                                                          of blister                      weather resistance                                                                           80   85   78   81   80   58    58    85                        absence or presence of                                                                       absence                                                                            absence                                                                            absence                                                                            absence                                                                            absence                                                                            presence                                                                            presence                                                                            absence                   bleeding                                                                      __________________________________________________________________________                   Comparative Application Example                                               9     10    11    12   13   14   15   16                       __________________________________________________________________________    Pigment dispersing agent No.                                                                 62    63    64    65   66   2    22   --                       Acrylic resin No.                                                                            AC-8  AC-9  AC-9  AC-9 AC-8 --   --   --                       Polyester resin No.                                                                          --    --    --    --   --   PE-2 PE-1 PE-2                     Formulation of dispersion paste                                               pigment dispersing agent                                                                     12.0  21.0  11.6   5.8  7.5  6.0  9.0 --                       acrylic resin  31.7  24.2  43.3  49.1 34.2 --   --   --                       polyester resin                                                                              --    --    --    --   --   36.7 34.2 41.7                     xylene         21.3  19.8  22.3  22.3 23.3 22.3 21.8 23.3                     ethyl cellosolve                                                                             --    --    --    --   --   --   --   --                       cellosolve acetate                                                                           20.0  20.0   4.0   4.0 20.0 20.0 20.0 20.0                     titanium dioxide JR 602                                                                      --    --    --    --   --   --   --   --                       carbon black FW-200                                                                          --    --    --    --   --   --   --   --                       Fosterperm Yellow-H3G                                                                        --    --    --    --   15.0 --   --   --                       Fastogen Blue-RGA                                                                            --    --    --    --   --   --   --   --                       Paliogen Maroon L3820                                                                        --    15.0  --    --   --   --   --   --                       Rubicron Red 500RG                                                                           15.0  --    --    --   --   --   --   --                       Paliotol Red L3670                                                                           --    --    --    --   --   --   --   --                       Noboperm Red F3RK-70                                                                         --    --    18.8  --   --   15.0 --   15.0                     Paliogen Violet L-5080                                                                       --    --    --    18.8 --   --   15.0 --                       Properties of paste                                                           amount of pigment                                                                            40    70    40    20   30   20   30   20                       dispersing agent added                                                        viscosity of dispersion                                                                      1,060 1,620 820   2,430                                                                              9,700                                                                              4,100                                                                              2,200                                                                              17,600                   paste (CP)                                                                    storage stability of                                                                         good  good  good  poor poor poor poor poor                     dispersion paste                                                              Formulation of paint                                                          dispersion paste                                                                             52.0  51.7  44.2  44.2 51.7 52.0 51.7 52.0                     acrylic resin  23.8  23.7  24.2  24.2 23.7 --   --   --                       polyester resin                                                                              --    --    --    --   --   23.8 23.7 23.8                     melamine resin 19.5  19.4  20.8  20.8 19.4 19.5 19.4 19.5                     leveling agent  0.6   0.6   0.6   0.6  0.6  0.6  0.6  0.6                     thinner         4.1   4.6  10.2  10.2  4.6  4.1  4.6  4.1                     Properties of paint film                                                      30° specular gloss                                                                    84    72    78    25   42   28   15   21                       humidity resistance                                                                          occurrence                                                                          occurrence                                                                          occurrence                                                                          glossless                                                                          glossless                                                                          good good good                                    of blister                                                                          of blister                                                                          of blister                                         weather resistance                                                                           62    68    65    68   78   89   90   60                       absence or presence of                                                                       presence                                                                            presence                                                                            presence                                                                            presence                                                                           presence                                                                           absence                                                                            absence                                                                            absence                  bleeding                                                                      __________________________________________________________________________

What is claimed is:
 1. A pigment dispersing agent consisting of aproduct obtained by reactingan amine compound having at least one aminogroup and/or imino group, a weight average molecular weight of about 60to about 30,000 and an amine value of about 50 to about 2,000 mg KOH/gwith an acrylic copolymer having a weight average molecular weight ofabout 2,000 to about 100,000 a hydroxy value of about 5 to about 200,and one of a glycidyl group, an acetoacetoxy group, and a cyclocarbonategroup in a functional group number of about 0.7 to about 3.0 on averageper molecule as a side chain, provided that 1 mol of glycidyl group isdeemed to be 1 mol of hydroxyl group when calculating the hydroxylvalue, the mol ratio of the amine compound to the acrylic copolymerbeing from 1:1 to 1:40 and the bridge between the amine compound aminoand/or imino nitrogen and the acrylic copolymer being ##STR14##depending on whether the copolymer contains a glycidyl group, anacetoacetoxy group, or a cyclocarbonate group, respectively.
 2. Thepigment dispersing agent of claim 1 wherein the acrylic copolymercontains a glycidyl group.
 3. The pigment dispersing agent of claim 1wherein the acrylic copolymer contains an acetoacetoxy group.
 4. Thepigment dispersing agent of claim 1 wherein the acrylic copolymercontains a cyclocarbonate group.